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CAS No. : | 723-46-6 | MDL No. : | MFCD00010546 |
Formula : | C10H11N3O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JLKIGFTWXXRPMT-UHFFFAOYSA-N |
M.W : | 253.27 | Pubchem ID : | 5329 |
Synonyms : |
Ro 4-2130;NSC 147832;Salimol;Rufol;RP-2145
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 62.99 |
TPSA : | 106.6 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.21 cm/s |
Log Po/w (iLOGP) : | 0.95 |
Log Po/w (XLOGP3) : | 0.89 |
Log Po/w (WLOGP) : | 2.26 |
Log Po/w (MLOGP) : | -0.15 |
Log Po/w (SILICOS-IT) : | 0.16 |
Consensus Log Po/w : | 0.82 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.25 |
Solubility : | 1.42 mg/ml ; 0.0056 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.71 |
Solubility : | 0.49 mg/ml ; 0.00193 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.77 |
Solubility : | 0.0434 mg/ml ; 0.000171 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.73 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H317-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | Stage #1: at 80℃; for 1 h; Stage #2: With acetic acid In water |
4-Amino-N- (5-methvl-isoxazol-3-vl)-benzenesulphonamide (STX608, XDS01099); The solution of N- (5-methylisoxazol-3-yl)-4-acetamidobenzenesulphonamid (3.4 g, 11.5 mmol) in 10percent NaOH solution (15 mL) was stirred at 80°C for 1h, cooled to rt and neutralized to pH 6 with acetic acid. The precipitate was washed with water, dried in vacuo to yield off-white solid (2,8 g, 96percent). Mp167-169°C (lit [29], 168-171°C) ; TLC single spot at Rf 0.39 (6percent methanol-DCM) ; HPLC purity > 99percent (tR 1.6 min in 4percent water- methanol) ;'H NMR (400 MHz, CD30D) : S 7.54 (2H, m, ArH), 6.63 (2H, m, ArH), 6.08 (1H, s, ArH), 2.30 (3H, s, CH3) ; FAB-MS 254 (MH+) ; FAB-HRMS calcd for C10H12N303S (MH+) 254.0599, found 254.0605. |
93% | With sodium hydroxide In water for 4 h; Reflux | To the intermediate 2 (2.53 mmol) suspended in water (15 mL)was added NaOH (31.7 mmol) and refluxed for 4 h to generate a yellow solution. This was acidified to pH 5.5 at 70-80 °C with 2 MHCl. After cooling it to room temperature precipitates formed werecollected, washed with H2O and dried to obtain the compound 3. 4.3.1 4-Amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide (3) Yield: 93percent; ESIMS m/z calcd for C10H11N3O3S [M + H]+, 254.06; found 254.11; 1H NMR (400 MHz, (CD3)2SO): δ 10.91 (bs, 1H), 7.46 (d, 2H, J = 8.76 Hz), 6.58 (d, 2H, J = 8.80 Hz), 6.08 (s, 1H), 6.07 (bs, 2H), 2.29 (s, 3H). 13C (100 MHz, (CD3)2SO): δ 170.33, 158.41, 153.76, 129.29, 124.58, 113.05, 95.76, 12.48. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | 4-Amino-N- (5-methvl-isoxazol-3-vl)-benzenesulphonamide (STX608, XDS01099); The solution of N- (5-methylisoxazol-3-yl)-4-acetamidobenzenesulphonamid (3.4 g, 11.5 mmol) in 10% NaOH solution (15 mL) was stirred at 80C for 1h, cooled to rt and neutralized to pH 6 with acetic acid. The precipitate was washed with water, dried in vacuo to yield off-white solid (2,8 g, 96%). Mp167-169C (lit [29], 168-171C) ; TLC single spot at Rf 0.39 (6% methanol-DCM) ; HPLC purity > 99% (tR 1.6 min in 4% water- methanol) ;'H NMR (400 MHz, CD30D) : S 7.54 (2H, m, ArH), 6.63 (2H, m, ArH), 6.08 (1H, s, ArH), 2.30 (3H, s, CH3) ; FAB-MS 254 (MH+) ; FAB-HRMS calcd for C10H12N303S (MH+) 254.0599, found 254.0605. | |
93% | With sodium hydroxide; In water; for 4h;Reflux; | To the intermediate 2 (2.53 mmol) suspended in water (15 mL)was added NaOH (31.7 mmol) and refluxed for 4 h to generate a yellow solution. This was acidified to pH 5.5 at 70-80 C with 2 MHCl. After cooling it to room temperature precipitates formed werecollected, washed with H2O and dried to obtain the compound 3. 4.3.1 4-Amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide (3) Yield: 93%; ESIMS m/z calcd for C10H11N3O3S [M + H]+, 254.06; found 254.11; 1H NMR (400 MHz, (CD3)2SO): delta 10.91 (bs, 1H), 7.46 (d, 2H, J = 8.76 Hz), 6.58 (d, 2H, J = 8.80 Hz), 6.08 (s, 1H), 6.07 (bs, 2H), 2.29 (s, 3H). 13C (100 MHz, (CD3)2SO): delta 170.33, 158.41, 153.76, 129.29, 124.58, 113.05, 95.76, 12.48. |
With sodium hydroxide; In water; at 104℃; for 2h;pH 14; | At the hydrolysis stage, the condensation product was added to a 12-fold amount of 10% aqueous sodium hydroxide solution, The pH value of the reaction solution should be 14, and then heated to 104 for 2h, cooled to below 85 , neutralized with concentrated hydrochloric acid to pH10, the maximum temperature should be At 75 C and then concentrated hydrochloric acid to adjust the pH to 4.6, cooled to below 25 C, centrifuged soil yellow crystalline sulfamethoxazole crude Product In the refining stage, the crude product was dissolved in about 12 times the mass of milk of lime and washed with charcoal (upper batch of activated carbon in washing water), heated to 70 C and allowed to stabilize at a pH of 10, plus activated charcoal at 85 C After 50min filtration, the filtrate was warmed to 80 C, a small amount of insurance and a small amount of hydrazine hydrate was added and immediately neutralized with 25% acetic acid to pH = 5.5 (isoelectric point), slowly cooled to 25 C, centrifuged, washed away Cl- and Ca2 + Plasma, dried to give sulfamethoxazole white crystalline powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | General procedure: Water (4 mL) and HBF4 (~48-50% aq. sol., 4 mL) was added to the aniline (0.50 mmol, 1.0 equiv.) and stirred for a couple of minutes at room temperature in an open reaction flask. NaNO2 (0.038 g,1.1 equiv.) in water (2.8 mL) was added dropwise at 0C and stirred for 30 minutes. To the cold solution of the resulting diazonium salt was added sat. aq. copper(II)sulfate (50 mL), followed by copper(I)oxide (1.0 equiv., 0.072 g), and stirred at room temperature for 30 minutes. The reaction mixture was extracted with CH2Cl2, dried (MgSO4)and evaporated in vacuo. The crude products were purified by silica gel chromatography.Potential hazard note: Diazonium compounds can be explosive, however, the risk is greatly reduced by following several rules for precaution.[17]Additional points that render the experimental procedure reported herein safer is that the diazonium salt is prepared in situ under dilute conditions and is not isolated, the reaction is performed open to air, the reaction temperature is 0C to ambient, HBF4-is used as the counterion in this procedure, and arene diazonium tetra-fluoroborates, in contrast to the chloride salts, are renowned in general for their enhanced thermal stability and shockin sensitivity. Nevertheless, care should always be taken when handling diazonium compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine;dmap; In dichloromethane; at 20 - 40℃; for 24 - 48h; | General Method for coupling 4-Amino-N- (5-methvl-isoxazol-3-vl)-benzenesulphonamide or 4-Amino-3-chloro-N- (5-methvlisoxazol-3-yl) benzenesulphonamide with arvlsulphonyl chloride (STX638, 642-644, 728, 729); To a solution arylsulphonyl chloride (1.1 eq. ) in DCM were added pyridine (1.3 eq. ) and catalytic amount of DMAP, followed by the amine (1 eq. ). The reaction mixture was stirred at rt or 40C under nitrogen for 24-48 h, then partitioned between DCM and water after TLC showed completion of the reaction. The organic layer was washed with 3% HCI solution and brine, dried over magnesium sulphate, and concentrated in vacuo to give crude product that was purified by recrystallization from ethyl acetate-DCM or by flash chromatography (ethyl acetate-DCM gradient elution) to give arylsulphonamide as white or off-white crystalline solid (Yield 40-80%).; N-r4-(5-Methyl-isoxazol-3-ylsulfamogl) phenyll-3', 4'-dimethoxY-benzenesulphonamide (STX638, XDS01105); White crystalline solid. TLC single spot at Rf 0.30 (6% methanol-DCM) ; HPLC purity as rotational isomers > 99% (tR 1.7 min in 4% water-methanol) ; 1H NMR (400 MHz, DMSO- d6): 5 11.3 (1H, s, NH), 10.8 (1H, s, NH), 7.71 (2H, d, J = 8.2 Hz, ArH), 7.41 (1H, m, ArH), 7.38 (3H, m, ArH), 7.07 (1H, d, J = 8.6 Hz, ArH), 6.08 (1H, s, ArH), 3.79 (3H, s, OCH3), 3.74 (3H, s, OCH3), 2.28 (3H, s, CH3) ; FAB-MS 454 (MH+) ; FAB-HRMS calcd for C18H20N307S2 (MH+) 454.0743, found 454.0746. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With nitric acid; In methanol; acetonitrile; | Example 7 Preparation of the <strong>[723-46-6]Sulfamethoxazole</strong> Nitrate Salt The compound is prepared by starting from a <strong>[723-46-6]Sulfamethoxazole</strong> solution (2 g, 7.9 mmoli) in methanol (100 ml), addition of a 65% nitric acid solution (0.500 ml) in acetonitrile (5 ml), following the procedure reported in Example 5. <strong>[723-46-6]Sulfamethoxazole</strong> nitrate as amorphous solid is obtained. Yield 60%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With acetic acid; In ethanol; for 1h;Reflux; | 4-(2-Hydroxy-3-methoxy benzylidenamine)-N-(5-methylisoxozaol-3-yl) benzenesulfonamide, (HL1) (1) was prepared by mixing(0.52 g, 2 mmol) of <strong>[723-46-6]sulfamethoxazole</strong> (SMZ) and (0.30 g, 2 mmol)of o-vanillin in 25 mL of absolute ethanol. Then, 2 drops of glacialacetic acid were added to make the medium acidic and the reactionmixture was stirred for 1 h. The resulting orange precipitate solidwas filtered and finally recrystallized from ethanol to give anorange crystal. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: 5.0 ml of 0.5M hydrochloric acid solution was placed into a 25ml volumetric flask. Then a sample of solution containing 0.4-14.0mugml-1 of sulphanilamide in final volume was added.Next 5.0 ml of 1.25x10-2M sodium nitrite solution was added into the flask. Obtained solution was stirred and cooled on an ice bath(~0 C) for 10 min. Then 1.0 ml of 1.25x10-3M Tropaeolin O solution was added into the flask. Obtained mixture was neutralized by adding of 2.5 ml of 1M sodium hydroxide solution and the pH value was adjusted to pH= 10.5 and distilled water was added to the full volume of 25ml. Then the solution was mixed thoroughly and the absorbance measurements (at room temperature ~20 C) were carried out against all corresponding reagents blank solution at 595nm in 1.0cm cuvettes. Sulphanilamide concentration was calculated using the methods of calibration curve and single-point standardization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate; In acetone; for 10h; | General procedure: Compound 12a (1 g, 3.56 mmol) and the appropriate sulfonamide (3.56 mmol) were stirred in dry acetone (50 ml) in the presence of anhydrous potassium carbonate (1 g, 4.83 mmol) for 10 h. The reaction mixture was then filtered while hot. Upon cooling, crystals separated out and were filtered and recrystallized from absolute ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In N,N-dimethyl-formamide; at 20℃; | General procedure: To a stirred solution of sulphonamide (2 mmol) in dimethylformamideat 0-5 C, chloro acetyl chloride (6 ml) wasadded dropwise and stirred at room temperature for 3-4 hoursby a magnetic stirrer. The reaction mixture was neutralizedwith triethylamine then the precipitate was filtered, washedwith cold water recrystallized from methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With triethylamine; In diethyl ether; benzene; at 100℃; | General procedure: A solution of 1 mmol of isocyanate 1-2 in 5 ml of benzene was added to 1 mmol of amine in 10 ml of dry benzene and 0.2 ml of saturated ether solution of catalyst trimethylamine in a 50 ml glass ampoule. This ampoule was sealed and heated at 100 C for 1.5-2 h. The ampoule was opened, the solvent was evaporated, and the residue was recrystallized from benzene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With sodium hydroxide; In water;pH 9 - 10; | The complexes were synthesized according to the procedure describedby Bult et al. [26], mixing 0.8 mmol of sulfonamide (SIGMA)in water and adding NaOH 1 M until total dissolution was achieved(pH = 9-10). To the resulting solution, 0.4 mmol of CoSO4 7H2O(Baker) dissolved in 20 mL of water were added dropwise. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | In acetonitrile; at 20℃; for 11.5h;Reflux; | General procedure: Sulphamethoxazole (SMX, I) (2 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriate isocyanate (2.1 mmol) was added in one portion. The solution was heated under reflux for 3.5 h and then stirred at ambient temperature for 8 h. The resulting crystals were filtered, washed with a small amount of MeCN and dried. The product was recrystallised from ethyl acetate (EtOAc) if necessary. |
16% | With triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 200℃; for 0.166667h;Microwave irradiation; | General procedure: 1-Adamantyl isocyanate (177 mg, 1.0 mmol), 4-aminosulfonamide (1.2 mmol) and triethylamine (502 muL, 3.6 mmol) were dissolved in a 1:1 mixture of THF/DMF (5 mL) in a microwave safe tube and stirred at 200 C for 10 min. The solvents were removed under reduced pressure and the crude residue was purified by reverse-phase flash column chromatography using a 0.1% formic acid in water to 0.1% formic acid in acetonitrile gradient. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In ethanol; acetic acid; at 20℃; for 3h; | General procedure: To a solution of compounds 4a-4c (7.6 mmol) in ethanol (15 mL) was added different substituted sulfonamide (7.6 mmol) and acetic acid (0.5 mL). The mixture was heated at room temperature for 3 h. A solid product was immediately formed which was filtered, washed with water. And the crude products were purified by recrystallization with ethanol, ethyl acetate and acetone(1:1:0.5) washed by ice-water (25 mL) for three times and dried to give a yellow solid product 5a-5r. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In ethanol; acetic acid; at 20℃; for 3h; | General procedure: To a solution of compounds 4a-4c (7.6 mmol) in ethanol (15 mL) was added different substituted sulfonamide (7.6 mmol) and acetic acid (0.5 mL). The mixture was heated at room temperature for 3 h. A solid product was immediately formed which was filtered, washed with water. And the crude products were purified by recrystallization with ethanol, ethyl acetate and acetone(1:1:0.5) washed by ice-water (25 mL) for three times and dried to give a yellow solid product 5a-5r. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In ethanol; acetic acid; at 20℃; for 3h; | General procedure: To a solution of compounds 4a-4c (7.6 mmol) in ethanol (15 mL) was added different substituted sulfonamide (7.6 mmol) and acetic acid (0.5 mL). The mixture was heated at room temperature for 3 h. A solid product was immediately formed which was filtered, washed with water. And the crude products were purified by recrystallization with ethanol, ethyl acetate and acetone(1:1:0.5) washed by ice-water (25 mL) for three times and dried to give a yellow solid product 5a-5r. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | General procedure: 1 eq. of the corresponding imidazolium bromide was dissolvedin distilled water and sent through an ion exchangecolumn (Merck ion exchange resin III). To this unstable hydroxidesalt in water the corresponding antibiotic or analgesicwas directly added, and the mixture was stirred for 2 hat room temperature. The solvent was evaporated under reducedpressure. The purity (especially halide residues) waschecked via ion chromatography. Since fosfomycin was onlyavailable as sodium salt, the neat compound was also producedvia ion exchange in water (Dowex 50WX8-100). Yield: 99 %. - Tg =30.2 C. - FT-IR (ATR) n (cm1)=673 (s), 739 (s), 939 (s), 1045 (m), 1090 (s), 1120 (s),1227 (m), 1267 (w), 1404 (m), 1458 (s), 1597 (m), 2961 (w), 3221 (w), 3333 (w), 3420 (w). - 1H NMR (300 MHz,[D6]DMSO): d = 9:20 (s, 1H, 2-H), 7.77 (s, 1H, 5-H), 7.70(s, 1H, 4-H), 7.31 - 7.28 (d, 2H, 16-H, 14-H), 6.45 - 6.42 (d,2H, 11-H, 13-H), 5.72 (s, 1H, 23-H), 5.32 (b, 2H, 17-H), 4.16(t, 2H, 7-H), 3.85 (s, 3H, 6-H), 2.08 (s, 3H, 27-H), 1.75 (m,2H, 8-H), 1.26 (m, 2H, 9-H), 0.89 (t, 3H, 10-H). - 13C{1H}NMR (75 MHz, [D6]DMSO): d = 166:00 (s, 24-C), 164.94(s, 22-C), 149.63 (s, 12-C), 136.61 (s, 2-C), 134.60 (s, 16-C,14-C), 123.53 (s, 5-C), 122.19 (s, 4-C), 112.22 (s, 11-C, 13-C), 97.07 (s, 23-C), 48.28 (s, 7-C), 35.54 (s, 6-C), 31.39 (s,8-C), 18.51 (s, 9-C), 13.30 (s, 27-C), 12.26 (s, 10-C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | General procedure: 1 eq. of the corresponding imidazolium bromide was dissolvedin distilled water and sent through an ion exchangecolumn (Merck ion exchange resin III). To this unstable hydroxidesalt in water the corresponding antibiotic or analgesicwas directly added, and the mixture was stirred for 2 hat room temperature. The solvent was evaporated under reducedpressure. The purity (especially halide residues) waschecked via ion chromatography. Since fosfomycin was onlyavailable as sodium salt, the neat compound was also producedvia ion exchange in water (Dowex 50WX8-100). Yield: 92 %. - Tg = 27 C. - FT-IR (ATR): n (cm1) =623 (m), 669 (s), 740 (m), 833 (m), 937 (m), 1043 (m),1092 (s), 1123 (s), 1165 (m), 1231 (m), 1269 (m), 1296 (w),1400 (m), 1458 (s), 1597 (m), 2852 (m), 2922 (m), 3102 (w),3148 (w), 3219 (w), 3337 (w). - 1H NMR (300 MHz, D2O):d = 9:27 (s, 1H, 2-H), 7.77 (s, 1H, 4-H), 7.70 (s, 1H, 5-H), 7.32 - 7.29 (d, 2H, 26-H=28-H), 6.45 - 6.42 (d, 2H, 23-H=25-H), 5.73 (s, 1H, 35-H), 5.32 (s, 2H, 29-H), 4.15 (t, 2H, 7-H),3.85 (s, 3H, 6-H), 2.09 (s, 3H, 39-H), 1.76 (m, 2H, 8-H), 1.23(b, 26H, 9-H-21-H), 0.85 (t, 3H, 22-H). - 13C{1H} NMR(75 MHz, D2O): d = 166:46 (s, 34-C), 165.16 (s, 36-C),149, 65 (s, 24-C), 136.70 (s, 2-C), 134.57 (s, 27-C), 127.28(s, 28-C=26-C), 123.56 (s, 4-C), 122.23 (s, 5-C), 112.22 (s,23-C=25-C), 96.95 (s, 35-C), 48.72 (s, 7-C), 35.69 (s, 6-C),31.29 (s, 8-C), 29.45 (s, 9-C), 29.05 (m, 10-C-18-C), 28.40(s, 19-C), 25.50 (s, 20-C), 22.09 (s, 21-C), 13.94 (s, 39-C),12.22 (s, 22-C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | General procedure: 1 eq. of the corresponding imidazolium bromide was dissolvedin distilled water and sent through an ion exchangecolumn (Merck ion exchange resin III). To this unstable hydroxidesalt in water the corresponding antibiotic or analgesicwas directly added, and the mixture was stirred for 2 hat room temperature. The solvent was evaporated under reducedpressure. The purity (especially halide residues) waschecked via ion chromatography. Since fosfomycin was onlyavailable as sodium salt, the neat compound was also producedvia ion exchange in water (Dowex 50WX8-100). Yield: 93 %. - Tg = 17.3 C. - FT-IR (ATR):n (cm1) = 671 (s), 743 (s), 795 (m), 833 (m), 937 (s), 1042(m), 1090 (s), 1121 (s), 1225 (s), 1267 (m), 1315 (m), 1398(m), 1456 (s), 1599 (s), 1649 (m), 2853 (m), 2930 (m), 3117(w), 3230 (m), 3337 (m), 3397 (m). - 1H NMR (300 MHz,[D6]DMSO): d = 9:19 (s, 1H, 2-H), 7.77 (s, 1H, 5-H), 7.70(s, 1H, 4-H), 7.32 - 7.29 (d, 2H, 20-H, 18-H), 6.45 - 6.42 (d, 2H, 15-H, 17-H), 5.74 (s, 1H, 27-H), 5.35 (s, 2H, 7-H), 4.15(t, 2H, 7-H), 3.85 (s, 3H, 6-H), 2.09 (s, 3H, 31-H), 1.76(m, 2H, 8-H), 1.24 (b, 10H, 9-H-13-H), 0.85 (t, 3H, 14-H). - 13C{1H} NMR (75 MHz, [D6]DMSO): d = 165:54(s, 28-C), 149.78 (s, 16-C), 136.60 (s, 2-C), 134.14 (s, 19-C), 127.37 (s, 20-C, 18-C), 123.59 (s, 5-C), 122.25 (s, 4-C), 112.23 (s, 15-C, 17-C), 99.04 (s, 26-C), 96.90 (s, 27-C),48.75 (s, 7-C),35.73 (s, 6-C), 31.17 (s, 8-C), 29.41 (s, 9-C),28.48 (s, 10-C), 28.34 (s, 11-C), 25.50 (s, 12-C), 22.06 (s,13-C), 13.69 (s, 31-C), 12.24 (s, 14-C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | General procedure: A substituted sulfonamide (1.0 mmol) was taken in a 100 mL beaker and treated with hydrochloric acid (1.0 mmol) and 2.0 mL distilled water and cooled the solution to 0-5 C. To this cold solution, 0.96 g, NaNO2, dissolved in water was added slowly. The diazonium salt thus obtained was treated with a solution containing 0.368 g curcumin in 5.0 mL KOH (0.5 M) solution. The products separated out as yellow solid which was filtered by Whatman filter paper No. 1 and dried at room temperature. The compounds were recrystallized in hot ethanol (Scheme 2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In ethanol; at 60℃; for 4h; | General procedure: In a 100 mL round bottom flask curcumin (1.0 mmol) and substituted sulfonamide (1.0 mmol) in 10 mL ethanol were refluxed on water bath for 3-4 h at 60 C. The reaction was monitored thin layer chromatography (TLC) (acetone: Hexane in 6:4 ratio). After completion of the reaction, contents were allowed to cool at room temperature and evaporated the solvent using rotary evaporator. The crude product was recrystallized from hot ethanol (Scheme 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With acetic acid; In ethanol; at 60℃; for 2h; | General procedure: A 100 mL round bottom flask was charged with curcumin (1.0 mmol), substituted sulfonamide (2.0 mmol) in 10 mL ethanol and 0.02 mL acetic acid as catalyst and refluxed on water bath for 4 h at 60 C, the reaction was monitored by thin layer chromatography (TLC) (acetone: Hexane in 6:4 ratio). After completion of the reaction, contents were allowed to cool at room temperature and evaporated the solvent using rotary evaporator. The crude product was recrystallized from hot ethanol (Scheme 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With potassium hydroxide; In water; at 20℃; for 1h; | The silver(I) complex with <strong>[723-46-6]sulfamethoxazole</strong> (Ag-SFM) was synthesized by the reaction of 5.0mL of an aqueous solution containing 4.0×10-4mol (0.1015g) of the <strong>[723-46-6]sulfamethoxazole</strong> (SFM) and 8.0×10-4mol (0.0476g) of KOH with 1.0mL of an aqueous solution containing 4.0×10-4mol (0.0685g) of AgNO3. The synthesis was carried out with stirring at room temperature. After 1h a white solid obtained was vacuum filtered, washed with cold water and dried in a desiccator under vacuum. Anal. Calc. for AgC10H10N3O3S: C, 33.3; H, 2.80; N, 11.7. Found: C, 32.1; H, 2.86; N, 11.1%. The yield of the synthesis was 70%. As observed for the Ag-SFT complex, the Ag-SFM is insoluble in dichloromethane, chloroform, acetonitrile, hexane, acetone, ethanol, methanol and water. It is also soluble and stable in DMSO. The UV-Vis spectrum of Ag-SFM complex shows a band centered at 269 nm with a molar absorptivity coefficient of 19874Lmol-1cm-1 in DMSO. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium hydroxide; In methanol; for 0.0416667h;pH 7 - 8;Microwave irradiation; | General procedure: The equimolar (1:1) ratio of methanolic solution of drug and methanolic solution of pyridoxal hydrochloride were mixed thoroughly and 0.1% methanolic KOH was added to adjust the pH of the solution within 7-8 and was then irradiated in the microwave oven by taking 3-4 ml solution. The reaction was completed in a short time (1-2 min) with higher yields showing clear coloured solution. The Schiff base ligands were isolated by crystallization after volume reduction by evaporation. The crystalline products were dried under vacuum or reduce pressure under anhydrous CaCl2and kept in a desiccator till further use. The progress of the reaction and purity of the products were monitored by TLC using silica gel G (yield: 73-89%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In acetonitrile; at 20℃; for 11.5h;Reflux; | General procedure: Sulphamethoxazole (SMX, I) (2 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriate isocyanate (2.1 mmol) was added in one portion. The solution was heated under reflux for 3.5 h and then stirred at ambient temperature for 8 h. The resulting crystals were filtered, washed with a small amount of MeCN and dried. The product was recrystallised from ethyl acetate (EtOAc) if necessary. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In acetonitrile; at 20℃; for 11.5h;Reflux; | General procedure: Sulphamethoxazole (SMX, I) (2 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriate isocyanate (2.1 mmol) was added in one portion. The solution was heated under reflux for 3.5 h and then stirred at ambient temperature for 8 h. The resulting crystals were filtered, washed with a small amount of MeCN and dried. The product was recrystallised from ethyl acetate (EtOAc) if necessary. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In acetonitrile; at 20℃; for 11.5h;Reflux; | General procedure: Sulphamethoxazole (SMX, I) (2 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriate isocyanate (2.1 mmol) was added in one portion. The solution was heated under reflux for 3.5 h and then stirred at ambient temperature for 8 h. The resulting crystals were filtered, washed with a small amount of MeCN and dried. The product was recrystallised from ethyl acetate (EtOAc) if necessary. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In acetonitrile; at 20℃; for 11.5h;Reflux; | General procedure: Sulphamethoxazole (SMX, I) (2 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriate isocyanate (2.1 mmol) was added in one portion. The solution was heated under reflux for 3.5 h and then stirred at ambient temperature for 8 h. The resulting crystals were filtered, washed with a small amount of MeCN and dried. The product was recrystallised from ethyl acetate (EtOAc) if necessary. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In acetonitrile; at 20℃; for 11.5h;Reflux; | General procedure: Sulphamethoxazole (SMX, I) (2 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriate isocyanate (2.1 mmol) was added in one portion. The solution was heated under reflux for 3.5 h and then stirred at ambient temperature for 8 h. The resulting crystals were filtered, washed with a small amount of MeCN and dried. The product was recrystallised from ethyl acetate (EtOAc) if necessary. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In acetonitrile; at 20℃; for 11.5h;Reflux; | General procedure: Sulphamethoxazole (SMX, I) (2 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriate isocyanate (2.1 mmol) was added in one portion. The solution was heated under reflux for 3.5 h and then stirred at ambient temperature for 8 h. The resulting crystals were filtered, washed with a small amount of MeCN and dried. The product was recrystallised from ethyl acetate (EtOAc) if necessary. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In acetonitrile; at 20℃; for 11.5h;Reflux; | General procedure: Sulphamethoxazole (SMX, I) (2 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriate isocyanate (2.1 mmol) was added in one portion. The solution was heated under reflux for 3.5 h and then stirred at ambient temperature for 8 h. The resulting crystals were filtered, washed with a small amount of MeCN and dried. The product was recrystallised from ethyl acetate (EtOAc) if necessary. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In acetonitrile; at 20℃; for 11.5h;Reflux; | General procedure: Sulphamethoxazole (SMX, I) (2 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriate isocyanate (2.1 mmol) was added in one portion. The solution was heated under reflux for 3.5 h and then stirred at ambient temperature for 8 h. The resulting crystals were filtered, washed with a small amount of MeCN and dried. The product was recrystallised from ethyl acetate (EtOAc) if necessary. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With trimethylamine; In diethyl ether; benzene; at 100℃;Sealed tube; | General procedure: A solution of 1 mmol of isocyanate 8 in 5 ml of benzene was added to 1 mmol of amine 9f, g in 10 ml of dry benzene and 0.2 ml of saturated ether solution of catalyst trimethylamine in a 50 ml glass ampoule. This ampoule was sealed and heated at 100 C for 1.5-2 h. The ampoule was opened, the solvent was evaporated, and the residue was recrystallized from benzene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | General procedure: To a stirred solution of compound 3 (0.98 mmol) in dry THF(10 mL) at 0 C under nitrogen was added DIPEA (1.13 mmol) followed by triphosgene (0.39 mmol) and continued stirring for 1 hand for 2 h at room temperature. At this point of time, respectiveamines (1.07 mmol) were added and allowed to stir at room temperaturefor 12 h. The reaction mixture was evaporated to drynessand diluted with water, extracted with EtOAc, dried over anhyd.Na2SO4 and concentrated under vacuum. The obtained residueswere purified with flash column chromatography using heptanes toEtOAc (20-40%) gradient elution to afford the compounds 4a-d inrespective yields. 4.4.1 4-(3-Benzylureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide (4a); Yield: 29%; ESIMS m/z calcd for C18H18N4O4S [M + H]+, 387.11; found 387.03; 1H NMR (400 MHz, (CD3)2SO): delta 11.22 (s, 1H), 9.08 (s, 1H), 7.70 (d, 2H, J = 8.92 Hz), 7.57 (d, 2H, J = 9.00 Hz), 7.35-7.24 (m, 5H), 6.82 (t, 1H, J = 5.96 Hz), 6.11 (s, 1H), 4.30 (d, 2H, J = 5.92 Hz), 2.29 (s, 3H). 13C (100 MHz, (CD3)2SO): delta 170.64, 158.14, 155.17, 145.47, 140.42, 131.22, 128.79, 128.56, 127.59, 127.26, 117.58, 95.81, 43.21, 12.51; HRMS (ES): m/z calcd for C18H18N4O4S [M + Na]+, 409.0941; found 409.0942. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | General procedure: To a stirred solution of compound 3 (0.98 mmol) in dry THF(10 mL) at 0 C under nitrogen was added DIPEA (1.13 mmol) followed by triphosgene (0.39 mmol) and continued stirring for 1 hand for 2 h at room temperature. At this point of time, respectiveamines (1.07 mmol) were added and allowed to stir at room temperaturefor 12 h. The reaction mixture was evaporated to drynessand diluted with water, extracted with EtOAc, dried over anhyd.Na2SO4 and concentrated under vacuum. The obtained residueswere purified with flash column chromatography using heptanes toEtOAc (20-40%) gradient elution to afford the compounds 4a-d inrespective yields. 4.4.2. 4-(3-(2-Hydroxybenzyl)ureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide (4b); Yield: 30%; ESIMS m/z calcd for C18H18N4O5S [M + H]+, 403.11; found 403.02; 1H NMR (400 MHz, (CD3)2SO): delta 11.21 (bs, 1H), 9.59 (s, 1H), 9.11 (s, 1H), 7.69 (d, 2H, J = 8.84 Hz), 7.55 (d, 2H, J = 8.84 Hz), 7.14 (d, 1H, J = 7.44 Hz), 7.10-7.06 (m, 1H), 6.81 (d, 1H, J = 7.96 Hz), 6.75 (t, 1H, J = 7.40 Hz), 6.64 (t, 1H, J = 5.82 Hz), 6.10 (s, 1H), 4.22 (d, 2H, J = 5.80 Hz), 2.28 (s, 3H). 13C (100 MHz, (CD3)2SO): delta 170.63, 158.14, 155.51, 155.23, 145.45, 131.18, 129.16, 128.58, 128.55, 126.01, 119.30, 117.47, 115.41, 95.81, 39.00, 12.51; HRMS (ES): m/z calcd for C18H18N4O5S [M + Na]+, 425.0890; found 425.0896. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | General procedure: To a stirred solution of compound 3 (0.98 mmol) in dry THF(10 mL) at 0 C under nitrogen was added DIPEA (1.13 mmol) followed by triphosgene (0.39 mmol) and continued stirring for 1 hand for 2 h at room temperature. At this point of time, respectiveamines (1.07 mmol) were added and allowed to stir at room temperaturefor 12 h. The reaction mixture was evaporated to drynessand diluted with water, extracted with EtOAc, dried over anhyd.Na2SO4 and concentrated under vacuum. The obtained residueswere purified with flash column chromatography using heptanes toEtOAc (20-40%) gradient elution to afford the compounds 4a-d inrespective yields. 4.4.3. 4-(3-(4-Hydroxyphenyl)ureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide (4c); Yield: 29%; ESIMS m/z calcd for C17H16N4O5S [M + H]+, 389.09; found 389.11; 1H NMR (400 MHz, (CD3)2SO): delta 11.25 (bs, 1H), 9.12 (s, 1H), 9.03 (s, 1H), 8.49 (s, 1H), 7.73 (d, 2H, J = 8.84 Hz), 7.60 (d, 2H, J = 8.88 Hz), 7.22 (d, 2H, J = 8.80 Hz), 6.69 (d, 2H, J = 8.80 Hz), 6.12 (s, 1H), 2.29 (s, 3H). 13C (100 MHz, (CD3)2SO): delta 170.68, 158.13, 153.41, 152.81, 145.06, 131.62, 130.96, 128.60, 121.26, 117.93, 115.72, 95.83, 12.51; HRMS (ES): m/z calcd for C17H16N4O5S [M + Na]+, 411.0734; found 411.0738. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | General procedure: To a stirred solution of compound 3 (0.98 mmol) in dry THF(10 mL) at 0 C under nitrogen was added DIPEA (1.13 mmol) followed by triphosgene (0.39 mmol) and continued stirring for 1 hand for 2 h at room temperature. At this point of time, respectiveamines (1.07 mmol) were added and allowed to stir at room temperaturefor 12 h. The reaction mixture was evaporated to drynessand diluted with water, extracted with EtOAc, dried over anhyd.Na2SO4 and concentrated under vacuum. The obtained residueswere purified with flash column chromatography using heptanes toEtOAc (20-40%) gradient elution to afford the compounds 4a-d inrespective yields. 4.4.4. 4-(3-Cyclohexylureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide (4d); Yield: 16%; ESIMS m/z calcd for C17H22N4O4S [M + H]+, 379.14; found 379.04; 1H NMR (400 MHz, (CD3)2SO): delta 11.20 (bs, 1H), 8.78 (s, 1H), 7.67 (d, 2H, J = 8.84 Hz), 7.52 (d, 2H, J = 8.88 Hz), 6.26 (d, 1H, J = 8.80 Hz), 6.09 (s, 1H), 3.47-3.45 (m, 1H), 2.28 (s, 3H), 1.80-1.77 (m, 2H), 1.66-1.63 (m, 2H), 1.55-1.52 (m, 1H), 1.34-1.26 (m, 2H), 1.21-1.13 (m, 3H). 13C (100 MHz, (CD3)2SO): delta 170.62, 158.16, 154.28, 145.53, 131.02, 128.57, 117.35, 95.81, 48.18, 33.19, 25.64, 24.74, 12.50; HRMS (ES): m/z calcd for C17H22N4O4S [M + Na]+, 401.1254; found 401.1262. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | General procedure: To a stirred solution of compound 3 (0.39 mmol) in dry THF(2 mL) at 0 C under nitrogen atmosphere was added thiophosgene(0.39 mmol) and continued stirring for 1 h. Reaction mixture waswarmed to room temperature and continued stirring for overnight.The solvent was evaporated to dryness and the residue was suspendedin 1,4-dioxane (3 mL), to this was added triethylamine(0.98 mmol) followed by respective amines (0.39 mmol) and stirredat reflux for 12 h. The reaction mixture was evaporated to drynessand the crude was purified by flash column chromatography using 1-5% MeOH in dichloromethane gradient elution to afford thecompounds 5a-d in respective yields. 4.5.1. 4-(3-Benzylthioureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide (5a); Yield: 29%; ESIMS m/z calcd for C18H18N4O3S2 [M + H]+, 403.09; found 402.96; 1H NMR (600 MHz, (CD3)2SO): delta 11.34 (bs, 1H), 9.99 (bs, 1H), 8.52 (bs, 1H), 7.77-7.74 (m, 4H), 7.36-7.34 (m, 4H), 7.28-7.26 (m, 1H), 6.13 (s, 1H), 4.74 (d, 2H, J = 4.86 Hz), 2.29 (s, 3H). 13C (100 MHz, (CD3)2SO): delta 180.96, 170.70, 158.13, 144.60, 138.88, 133.77, 128.81, 128.01, 127.51, 121.86, 95.84, 47.64, 12.54; HRMS (ES): m/z calcd for C18H18N4O3S2 [M + Na]+, 425.0713; found 425.0709. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | General procedure: To a stirred solution of compound 3 (0.39 mmol) in dry THF(2 mL) at 0 C under nitrogen atmosphere was added thiophosgene(0.39 mmol) and continued stirring for 1 h. Reaction mixture waswarmed to room temperature and continued stirring for overnight.The solvent was evaporated to dryness and the residue was suspendedin 1,4-dioxane (3 mL), to this was added triethylamine(0.98 mmol) followed by respective amines (0.39 mmol) and stirredat reflux for 12 h. The reaction mixture was evaporated to drynessand the crude was purified by flash column chromatography using 1-5% MeOH in dichloromethane gradient elution to afford thecompounds 5a-d in respective yields. 4.5.2. 4-(3-(2-Hydroxybenzyl)thioureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide (5b); Yield: 42%; ESIMS m/z calcd for C18H18N4O4S2 [M + H]+, 419.08; found 419.00; 1H NMR (600 MHz, (CD3)2SO): delta 11.33 (bs, 1H), 9.99 (bs, 1H), 9.66 (bs, 1H), 8.26 (bs, 1H), 7.80-7.73 (m, 4H), 7.19 (d, 1H, J = 7.32 Hz), 7.13-7.09 (m, 1H), 6.84 (d, 1H, J = 7.84 Hz), 6.77 (t, 1H, J = 7.44 Hz), 6.13 (s, 1H), 4.63 (d, 2H, J = 4.48 Hz), 2.29 (s, 3H). 13C (100 MHz, (CD3)2SO): delta 180.57, 170.65, 158.22, 155.64, 144.73, 133.63, 129.65, 128.81, 127.95, 124.40, 121.46, 119.27, 115.39, 95.86, 43.48, 12.54; HRMS (ES): m/z calcd for C18H18N4O4S2 [M + Na]+, 441.0662; found 441.0667. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | General procedure: To a stirred solution of compound 3 (0.39 mmol) in dry THF(2 mL) at 0 C under nitrogen atmosphere was added thiophosgene(0.39 mmol) and continued stirring for 1 h. Reaction mixture waswarmed to room temperature and continued stirring for overnight.The solvent was evaporated to dryness and the residue was suspendedin 1,4-dioxane (3 mL), to this was added triethylamine(0.98 mmol) followed by respective amines (0.39 mmol) and stirredat reflux for 12 h. The reaction mixture was evaporated to drynessand the crude was purified by flash column chromatography using 1-5% MeOH in dichloromethane gradient elution to afford thecompounds 5a-d in respective yields. 4.5.4. 4-(3-Cyclohexylthioureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide (5d); Yield: 45%; ESIMS m/z calcd for C17H22N4O3S2 [M + H]+, 395.12; found 395.09; 1H NMR (600 MHz, (CD3)2SO): delta 11.32 (bs, 1H), 9.72 (bs, 1H), 8.03 (bs, 1H), 7.74 (s, 4H), 6.14 (s, 1H), 4.09 (m, 1H), 2.30 (s, 3H), 1.92-1.90 (m, 2H), 1.70-1.68 (m, 2H), 1.58-1.56 (m, 1H), 1.33-1.16 (m, 5H). 13C (100 MHz, (CD3)2SO): delta 179.25, 170.71, 158.09, 144.87, 133.29, 127.95, 121.29, 95.83, 52.69, 32.05, 25.58, 24.90, 12.53; HRMS (ES): m/z calcd for C17H22N4O3S2 [M + Na]+, 417.1026; found 417.1030. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | To a stirred solution of compound 3 (7.89 mmol) in dry THF (20 mL) at 0 C under nitrogen, was added NaH (8.28 mmol) and continued stirring for 30 min. To this reaction mixture acryloyl chloride (8.28 mmol) was added drop wise and stirred at same temperature for 1 h and 4 h at room temperature. Excess NaH was quenched with little methanol water mixture (1:1). The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated. The crude was purified by column chromatography using 10-30% EtOAc in heptanes as an eluent to obtain compound 12. 4.12.1 N-(4-(N-(5-Methylisoxazol-3-yl)sulfamoyl)phenyl)acrylamide (12) Yield: 47%; ESIMS m/z calcd for C13H13N3O4S [M + H]+, 308.07; found 308.07; 1H NMR (400 MHz, (CD3)2SO): delta 11.37 (bs, 1H), 11.00 (bs, 1H), 7.92 (d, 2H, J = 8.88 Hz), 7.80 (d, 2H, J = 8.88 Hz), 6.61-6.54 (m, 1H), 6.29 (dd, 1H, J = 17.40, 1.80 Hz), 6.13 (s, 1H), 5.80 (dd, 1H, J = 10.16, 1.82 Hz), 2.29 (s, 3H). 13C (100 MHz, (CD3)2SO): delta 170.70, 164.26, 158.02, 143.94, 133.71, 132.00, 128.45, 128.29, 119.60, 95.85, 12.52. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With acetic acid; at 120℃; for 0.166667h; | General procedure: To suspension of phenyl pyrazolocurcumin derivative 6 (0.44 g,1 mmol) in glacial acetic acid (1.5 mL), sulfathiazole (7a) (0.44 g,2 mmol), <strong>[723-46-6]sulfamethoxazole</strong> (7b) (0.50 g, 2 mmol) or sulfadiazine(7c) (0.50 g, 2 mmol) was added. The reaction mixture was heatedin an oil bath at 120 C for 10 min and then left to cool at roomtemperature. The fused result was triturated with absolute ethanol(10 mL) and then heated again under reflux for 20 min. The solidproduct obtained upon cooling was collected by filtration and crystallizedfrom appropriate solvent. 2.1.3.2 N,N'-(((1E,1'E)-(1-Phenyl-1H-pyrazole-3,5-diyl)bis(ethene-2,1-diyl))bis(3-methoxy-4,1-phenylene))bis(4-((5-methylisoxazol-3-yl)amino)benzenesulfonamide) (8b) Brown crystals from absolute ethanol, yield 0.55 g (61%); mp 149-151 C; IR (KBr, cm-1): nu 3377-3141 (broad peak, NH groups), 2927 (CH3), 1597 (C=C), 1506 (C=N), 1148 (SO2). 1H NMR (CDCl3, ppm): delta = 3.35 (s, 6H, CH3), 3.73 (s, 6H, 2OCH3), 5.88 (s, 1H, C4-H pyrazole proton), 6.19 (d, 2H,C2-H and C8-H), 6.61 (d, 2H,C1-H and C7-H), 6.74-7.68 (m, 21H, aromatic H and isoxazole protons), 8.30 (s, 2H, 2NH, D2O-exchangeable), 11.50 (s, 2H, 2NH, D2O-exchangeable). MS (EI) m/z (%): 911 (M+?, 24%), 577 (5), 565 (7), 537 (2), 313 (4), 236 (3), 81 (7), 64 (100), 57 (14). Calc for C47H42N8O8S2 (911.020): C, 61.96; H, 4.65; N, 12.30; S, 7.04, found: C, 61.70; H, 4.37; N, 11.98; S, 6.78%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | <strong>[723-46-6]Sulfamethoxazole</strong> (0.5 g, 1.97 mmol) was dissolved in aqueous-HCl (5% HCl solution, 15 ml) (Scheme 1) and was allowed to reactwith an aqueous solution of NaNO2 (1.0 g, 5 ml) solution at 0-5 C,followed by coupling with acetylacetone (0.198 g, 1.97 mmol) inthe presence of sodium acetate (2.0 g) to maintain the pH at 5.5-6.5 in water, according to the literature procedure [25]. A brightyellow precipitate was obtained, which was filtered and dried atroom temperature. It was then recrystallized by slow evaporationof a hot alcoholic solution and its purity was checked by TLC.Yield: 82%. M.P.: 205 ± 1 C. Microanalytical data for HL; Anal.Calc. for C15H16N4O5S: C, 49.44; H, 4.43; N, 15.38; S, 8.80; Found:C, 49.34; H, 4.33; N, 15.31; S, 8.75%. FT-IR bands (KBr pellet,cm1): m(NN), 1427; m(CN), 1621; m(CO), 1686; m(O-H),3451; m(S-O), 1161. 1H NMR data (DMSO-d6, ppm): 6.12 (4H, s),11.38 (6N-H, s), 7.70 (8,9H, d, J = 8.79 Hz), 7.83 (7,10H, d,J = 8.73 Hz), 13.44 (11-O-H, s), 2.27 (5-CH3, s), 2.42 (11-CH3, s),2.41 (12-C H3, s). [M+H+], m/z: 365.09 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | General procedure: A cold solutionof 2.5 mL of sodium nitrite (0.207 g, 3 mmol) was added drop wise to ice-cold solution of twelve different individual substituted aromatic amines in conc. HCl and water in equal proportion. The temperature of the reaction was maintained within a range of 0-5 C. The diazotized solutions poured into an ice cold solution of 2-thiobarbituric acid in 10 % (20 mL) sodium hydroxide solution. The coloured products obtained were filtered, washed with water and dried. Finally obtained products recrystallized from ethanol. The progress of reaction was monitored by TLC using suitable solvent system. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With sodium hydroxide; In methanol; ethanol; for 3h;pH 7.8 - 8;Reflux; | General procedure: A general procedure was followed for the preparation of thecomplexes using metal acetate and the Schiff base. An ethanolicsolution (20 mL) of sulfa drug (2 mmol) was mixed with (0.22 g,2 mmol) of o-vanillin in 20 mL of methanol. Then, (1 mmol) metalacetate was dissolved in hot methanol and added to the mixture.Then, a few drops of sodium hydroxide (1 M) were added to resultingsolution to adjust the pH to 7.8-8.0. Then, the solution washeated under reflux for 3 h. The reaction mixture was concentratedby evaporation, and the precipitate of metal complexes were collectedby filtration, washed with hot water, ethanol and finallywith small portion of diethyl ether to extract all organic impurities. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With sodium hydroxide; In methanol; ethanol; for 3h;pH 7.8 - 8;Reflux; | General procedure: A general procedure was followed for the preparation of thecomplexes using metal acetate and the Schiff base. An ethanolicsolution (20 mL) of sulfa drug (2 mmol) was mixed with (0.22 g,2 mmol) of o-vanillin in 20 mL of methanol. Then, (1 mmol) metalacetate was dissolved in hot methanol and added to the mixture.Then, a few drops of sodium hydroxide (1 M) were added to resultingsolution to adjust the pH to 7.8-8.0. Then, the solution washeated under reflux for 3 h. The reaction mixture was concentratedby evaporation, and the precipitate of metal complexes were collectedby filtration, washed with hot water, ethanol and finallywith small portion of diethyl ether to extract all organic impurities. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With triethylamine; In toluene; at 200℃; for 2h;Sealed tube; High pressure; | General procedure: General procedures were followed for the reaction of ammonia with cantharidine and the other acid anhydride. These compounds were prepared according to similar procedures, and the reactions took place in high-pressure tubes (Buechi Glasuster 0032, Zuerich, Switzerland). Cantharidin or acid anhydrides were added to a tube containing 3 mL of dry toluene and triethylamine (TEA), and the solution was stirred and heated to ca. ~200C. After being stirred for 2 h, the mixture was evaporated, and the residual mass was purified by column chromatography on silica gel and recrystallized from methanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium carbonate; In ethanol; for 24h;Reflux; | General procedure: A mixture of 1-chlorophthalazine 3 (1g, 6mmol), the appropriate benzenesulfonamide (6mmol) and anhydrous potassium carbonate (12mmol) in ethanol (10ml) was heated under reflux for 24h. The mixture was poured onto ice-cooled water and neutralized with concentrated hydrochloric acid. The separated solid was filtered off and crystallized from the appropriate solvent. 4.1.1.3 N-(5-Methylisoxazol-3-yl)-4-(phthalazin-1-ylamino)benzenesulfonamide (5c) M.p. 240-243 C, yield: 85%. IR numax cm-1: 3388(NH), 3070 (aromatic CH), 2924 (Aliphatic CH), 1319, 1161 (SO2). 1H NMR (DMSO-d6): 300 MHz, delta = 2.30 (s, 3H, CH3), 6.16 (s, 1H, CH isoxazole), 7.86-8.17 (m, 7H, ArH + NH), 8.23 (d, 1H, J = 7.8 Hz, CH-5 phthalazine), 8.8 (d, 1H, J = 7.5 Hz, CH-8 phthalazine), 9.44 (s, 1H, CH-4 phthalazine),11.15 (s, 1H, SO2NH, exchanged by D2O). 13C NMR (75 MHz) delta = 12.0 (CH3), 95.3 (C-4 isoxazole), 119.9, 121.0, 123.3, 127.8, 128.1, 128.7, 131.2, 133.7, 134.1 (aromatic Cs), 143.9 (C-4 phthalazine), 148.6 (C-1 phenyl), 152.7 (C-3 isoxazole), 157.5 (C-1 phthalazine), 170.1(C-5 isoxazole). MS m/z: 381 [M+]. Anal. Calcd. for C18H15N5O3S (381.41): C, 56.68; H, 3.96; N, 18.36. Found: C, 56.73; H, 3.91; N, 18.57. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | General procedure: Each 4-aminobenzenesulfonamide (3.0 mmol) was added in asolution of concentrated sulfuric acid (0.5 mL) and H2O (3.0 mL)and then cooled to 0 C in an ice bath. A solution of NaNO2 (3.0mmol) in water (2.1 mL) was added dropwise to the reaction andleft stirring for 10 min. After a color change to a yellowish toneand appearance of foam in the medium, solid urea (150 mg) wasadded followed by NaN3 solution (9.0 mmol, 1.5 eq) in H2O (3.2mL) dropwise. Finally, after stirring for few minutes each reactionwas filtered through Buchner funnel and washed subsequentlywith 5% NaHCO3 and H2O. Each obtained product was dried underreduced pressure and analyzed by TLC, being verified at increasedretention factors (Rf) if compared to the corresponding startingmaterials. Compounds 8-14 were obtained in corresponding yieldsof 38% (8), 45% (9), 91% (10), 52% (11), 42,5% (12), 40% (13) and 76%(14). 1H NMR and IR [2100 cm1 (N3)] (2100 cm1) analysis of 8-14 were in accordance with the literature.28 | |
82% | With sodium azide; tert.-butylnitrite; In 1,4-dioxane; water; at 50℃; for 0.333333h;Microwave irradiation; | General procedure: Sodium azide (78 mg, 1.20 mmol, 3 equiv.) wasintroduced in a microwave flask equipped with a stirringbar and solubilized with water (150 muL). To this solution,the remaining reagents were added in the following order: solvent reaction (1 mL), 4-aminobenzenesulfonamide (16-22) (0.4 mmol, 1 equiv.) and tert-butyl nitrite(t-BuONO). The mixture was stirred and heated undermicrowave radiation at 150 W. The reaction was followedby TLC and after completion, the reaction mixture waspartitioned between hexane and EtOAc. The aqueousphase was extracted with EtOAc (3 times), and the organicphase was dried over Na2SO4, filtered and concentrated.The product was obtained after flash chromatographyon a Biotage Horizon, using 12 mm flash cartridge,flow 8 mL min-1; hexane/EtOAc; gradient 0-40% and40%-40% (v/v). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; isopropyl alcohol; | 0.368 g of sulfamethoxazole (1 .453 mmol) and 0.259 g of L-<strong>[3081-61-6]theanine</strong> (1 .487 mmol) were weighed directly into the bowl of an agate mortar, and wetted with 70% isopropanol to form a moderately thick slurry. The slurry was thoroughly ground at the time of mixing, and then periodically re-ground until the contents were dry. The XRPD pattern of the product is shown in Figure 28a, while the FTIR spectrum is shown in Figure 28b. The DSC melting endotherm of the product was characterized by a peak maximum at 169C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In acetonitrile; at 20℃;Reflux; | General procedure: <strong>[723-46-6]Sulfamethoxazole</strong> 1 (1 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriateisocyanate (1.1 mmol) was added in one portion. The solution was heated under reflux for 3 h and thenstirred at ambient temperature overnight. The resulting crystals were filtered, washed with a smallvolume of MeCN and dried. The product was recrystallized from ethyl acetate (EtOAc) if necessary [1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In acetonitrile; at 20℃;Reflux; | General procedure: <strong>[723-46-6]Sulfamethoxazole</strong> 1 (1 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriateisocyanate (1.1 mmol) was added in one portion. The solution was heated under reflux for 3 h and thenstirred at ambient temperature overnight. The resulting crystals were filtered, washed with a smallvolume of MeCN and dried. The product was recrystallized from ethyl acetate (EtOAc) if necessary [1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In acetonitrile; at 20℃;Reflux; | General procedure: <strong>[723-46-6]Sulfamethoxazole</strong> 1 (1 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriateisocyanate (1.1 mmol) was added in one portion. The solution was heated under reflux for 3 h and thenstirred at ambient temperature overnight. The resulting crystals were filtered, washed with a smallvolume of MeCN and dried. The product was recrystallized from ethyl acetate (EtOAc) if necessary [1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In acetonitrile; at 20℃;Reflux; | General procedure: <strong>[723-46-6]Sulfamethoxazole</strong> 1 (1 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriateisocyanate (1.1 mmol) was added in one portion. The solution was heated under reflux for 3 h and thenstirred at ambient temperature overnight. The resulting crystals were filtered, washed with a smallvolume of MeCN and dried. The product was recrystallized from ethyl acetate (EtOAc) if necessary [1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In acetonitrile; at 20℃;Reflux; | General procedure: <strong>[723-46-6]Sulfamethoxazole</strong> 1 (1 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriateisocyanate (1.1 mmol) was added in one portion. The solution was heated under reflux for 3 h and thenstirred at ambient temperature overnight. The resulting crystals were filtered, washed with a smallvolume of MeCN and dried. The product was recrystallized from ethyl acetate (EtOAc) if necessary [1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In acetonitrile; at 20℃;Reflux; | General procedure: <strong>[723-46-6]Sulfamethoxazole</strong> 1 (1 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriateisocyanate (1.1 mmol) was added in one portion. The solution was heated under reflux for 3 h and thenstirred at ambient temperature overnight. The resulting crystals were filtered, washed with a smallvolume of MeCN and dried. The product was recrystallized from ethyl acetate (EtOAc) if necessary [1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In acetonitrile; at 20℃;Reflux; | General procedure: <strong>[723-46-6]Sulfamethoxazole</strong> 1 (1 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriateisocyanate (1.1 mmol) was added in one portion. The solution was heated under reflux for 3 h and thenstirred at ambient temperature overnight. The resulting crystals were filtered, washed with a smallvolume of MeCN and dried. The product was recrystallized from ethyl acetate (EtOAc) if necessary [1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 24h; | Sulfamethoxazole 1 (1 mmol) was dissolved in dry acetonitrile (5 mL), then N,Ndiisopropylethylamine(2 mmol) followed by <strong>[18342-66-0]2,5-dioxopyrrolidin-1-yl methylcarbamate</strong> (1.5 mmol)was added. The solution was stirred for 24 h. The resulting crystals were filtered, washed with a smallvolume of MeCN and dried. The product was recrystallized from EtOAc if necessary. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In acetonitrile; at 20℃;Reflux; | General procedure: <strong>[723-46-6]Sulfamethoxazole</strong> 1 (1 mmol) was dissolved in dry acetonitrile (MeCN, 6 mL) and appropriateisocyanate (1.1 mmol) was added in one portion. The solution was heated under reflux for 3 h and thenstirred at ambient temperature overnight. The resulting crystals were filtered, washed with a smallvolume of MeCN and dried. The product was recrystallized from ethyl acetate (EtOAc) if necessary [1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In acetonitrile; at 20℃; for 2h; | <strong>[723-46-6]Sulfamethoxazole</strong> 1 (1 mmol) was dissolved in MeCN (6 mL) and oxalyl chloride (0.5 mmol) wasadded in one portion. The mixture was stirred for 2 h at room temperature. The resulting crystalswere filtered, washed with a small volume of MeCN and dried. The product was recrystallized fromtetrahydrofuran/hexane.N1,N2-Bis{4-[N-(5-methylisoxazol-3-yl)sulfamoyl]phenyl}oxalamide (3). White solid; yield 84%; m.p. > 300 C(decomp.). IR: 3344 (N-H), 1690 (C=O). 1H-NMR (300 MHz, DMSO): delta 11.42 (2H, s, CONH), 11.26 (2H,s, SO2NH), 8.07-8.01 (4H, m, H2, H6), 7.89-7.82 (4H, m, H3, H5), 6.13 (2H, d, J = 1.0 Hz, isoxazole), 2.28(6H, d, J = 1.1 Hz, CH3). 13C-NMR (75 MHz, DMSO): delta 170.54, 158.88, 157.69, 142.04, 134.93, 128.08,120.82, 95.61, 12.28. Anal. Calcd. for C22H20N6O8S2 (560.56): C, 47.14; H, 3.60; N, 14.99. Found: C,47.40; H, 3.51; N, 15.11. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Triphosgene (0.4 mmol) was dissolved in anhydrous dichloromethane (DCM; 5 mL) under argonatmosphere and decylamine (1.01 mmol) in dry DCM (3 mL) was added dropwise. This mixture wasstirred for 30 min at room temperature and then treated with triethylamine (2.1 mmol) in dry DCM(3 mL). After 30 min, a solution of <strong>[723-46-6]sulfamethoxazole</strong> 1 (1.01 mmol) in 5 mL of dry MeCN was added.The reaction mixture was stirred for 12 h at room temperature. Then 1 mL of glacial acetic acid wasadded and the reaction mixture was stirred for additional 2 h. The mixture was evaporated to dryness.After addition of 10 mL of MeCN, the suspension was let to stay overnight. The resulting crystals werefiltered, washed with a small volume of diethylether and dried to obtain the final product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Aliquots of sulfonamide derivative solutions (sulfanilamide, sulfamethoxazole,sulfamethiazole, sulfathiazole, sulfacetamide,Ssulfamerazine, sulfadiazine, sulfadimethoxine) ranging from 0.1-1.0 mL (10 mug mL-1) were transferred into each of the series of10 mL flasks, 1 mL of sodium (1% w/v) and 1 mL of 1 M hydrochloricacid were added with swirling at room temperature. After 5 min,1 mL of sulfamic acid (2% w/v) and 1 mL of <strong>[1465-25-4]N-(1-naphthyl)ethylenediamine dihydrochloride</strong> (1% w/v) were added withswirling. The volumes were adjusted to the mark with distilledwater, and then the solutions were mixed thoroughly. The absorbanceof the light pink colored solutions was measured at 536 nmagainst the reagent blank. Fig. 2 shows a picture of a gradient of concentrationsof the pink colored solutions tested. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | General procedure: Two sulfamethoxazolyl-azo-phenols were synthesized following identical procedure. Detail of synthesis of4-((2-hydroxy-5-methoxyphenyl)diazenyl)-N-(5-methylisoxazol-3-yl)benzene sulfonamide (1a) is given below.Upon addition of cold sodium nitrite (0.3 g, 5 ml) solutionto acidic solution (3 N HCl, 15 ml) of <strong>[723-46-6]sulfamethoxazole</strong>(0.61 g, 2.4 mmol) at 0-5C synthesized orange sulfamethoxazolyl diazonium (SMX-N=N-+) ion. To cold alkaline (1.8 g, NaOH) solution of p-methoxyphenol(0.30 g, 2.40 mmol) orange acidic suspension of SMX-N=N-+ was added and stirred. The pH of the reaction mixture was checked by litmus paper. An orange red precipitate appeared at pH 7 and filtered, washed with water, and driedin-vacuo. The products were crystallized from hot aqueous methanol(2:1, v/v) mixture. Needle shaped bright crystals were isolated, and purity was tested by TLC. Further purification was carried out by column chromatography (silicagel, 60-120 mesh) and the desired products were eluted with chloroform-ethylacetate (9:1, v/v) mixture. Slow evaporation of orange eluent had separated crystals; purity was checked by TLC and found single spot; yield, 0.76 g(82%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | General procedure: Two sulfamethoxazolyl-azo-phenols were synthesized following identical procedure. Detail of synthesis of4-((2-hydroxy-5-methoxyphenyl)diazenyl)-N-(5-methylisoxazol-3-yl)benzene sulfonamide (1a) is given below.Upon addition of cold sodium nitrite (0.3 g, 5 ml) solutionto acidic solution (3 N HCl, 15 ml) of <strong>[723-46-6]sulfamethoxazole</strong>(0.61 g, 2.4 mmol) at 0-5C synthesized orange sulfamethoxazolyl diazonium (SMX-N=N-+) ion. To cold alkaline (1.8 g, NaOH) solution of p-methoxyphenol(0.30 g, 2.40 mmol) orange acidic suspension of SMX-N=N-+ was added and stirred. The pH of the reaction mixture was checked by litmus paper. An orange red precipitate appeared at pH 7 and filtered, washed with water, and driedin-vacuo. The products were crystallized from hot aqueous methanol(2:1, v/v) mixture. Needle shaped bright crystals were isolated, and purity was tested by TLC. Further purification was carried out by column chromatography (silicagel, 60-120 mesh) and the desired products were eluted with chloroform-ethylacetate (9:1, v/v) mixture. Slow evaporation of orange eluent had separated crystals; purity was checked by TLC and found single spot; yield, 0.76 g(82%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With pyridine; In N,N-dimethyl-formamide;Reflux; | General procedure: A mixture of equimolar amounts (0.01 mol, 4.5 g) of ofbenzoxazinone derivative (6) and appropriate sulpha drug(0.01 mol) in DMF (10 mL) containing few drops of pyridinewas refluxed for 4 h. The reaction mixture was pouredover crushed ice, few drops of HCl was added and theseparated solid product was filtered, dried and recrystallizedfrom ethanol to give: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With pyridine; In N,N-dimethyl-formamide; for 4h;Reflux; | General procedure: A mixture of equimolar amounts (0.01 mol, 3.7 g) of2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetyl chloride (1) and appropriate sulpha drug (0.01 mol)in DMF (10 mL) containing few drops of pyridine wasrefluxed for 4 h. The reaction mixture was poured overcrushed ice, few drops of HCl was added and the separatedsolid product was filtered, dried and recrystallized fromethanol to give: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11.7% | With potassium hydroxide; In dichloromethane; at 40℃; for 9h; | Sulfamethoxazole (12.6 g, 0.05 mol)Potassium hydroxide (2.8 g, 0.05 mol) in dichloromethane solution of intermediate III,Was loaded into a 150 ml three-neck reaction flask,The reaction was stirred at 40 C for 9 hours,A solution of the sulfonamidomethyl isoxazole truncated dendrites derivatives in dichloromethane.Sulfadiazine was used to shorten the solution of the dorsalin derivative in methylene chloride,Washed with 0.1 M NaOH solution,Collecting organic layer,The organic layer was washed with 0.1 M HCl solution,Collecting water,Adjust the PH value to neutral,The organic layer was extracted with dichloromethane,Vacuum drying of dichloromethane,Sulfamethyl isoxazole Truncated Tyrone Derivatives3.7 g (yield 11.7%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | In ethanol; at 80℃; for 12h; | The Schiff base BA-SMX was synthesized by condensation of <strong>[723-46-6]sulfamethoxazole</strong> (SMX) and 4-(dimethylamino)benzaldehyde (BA). An ethanol solution of SMX (1mmol) was mixed with 1mmol of BA in ethanol. The mixture was stirred and refluxed at 80 C during 12 h and theprogress was followed by TLC. On completion, the reaction mixture was cooled and the yellow solid formed was isolated by filtration and washed with cool ethanol. The solid was re-crystallized from hot ethanol. Suitable crystals for XRD measurements were obtained by slow evaporation of a methanol solution of BA-SMX (See Scheme 1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With acetic acid; at 100℃; for 3h; | The intermediate 2 was refluxed with <strong>[723-46-6]sulfamethoxazole</strong>, a commercially available sulfa drug in acetic acid for 3?h. The reaction mixture became a clear solution in the beginning and started precipitating the product after 10?min. The product was filtered and washed with water to remove inorganic impurities. The product was recrystallized with acetone. Yield: 76%; m.p. 240-242?C; IR (KBr, cm-1): 3373, 3103(N-H), 3034(aromatic C-H stretch), 1622(C=N), 1315(asy. SO2), 1147(sym. SO2). 1H NMR (dmso-d6) delta: 10.16[s, 1H, NH], 8.66[s, 1H, Ar-H], 8.51[s, 1H, Ar-H], 8.08-8.10[d, 2H, J?=?8?Hz, Ar-H], 7.82-7.87[t, 4H, Ar-H], 7.65-7.67[d, 1H, J?=?4.8?Hz, Ar-H], 6.15[s, 1H, oxazole], 2.28[s, 1H, -CH3]. 13C NMR (dmso-d6) delta: 162.2, 158.2, 154.9, 153.6, 149.7, 144.6, 133.5, 132.4(2), 127.6, 127.3, 125.9, 122.2, 120.2(2), 116.3, 104.4, 10.92. ESI-MS (m/z): 382.0974(M+1). Anal. calcd (%) for C18H15N5SO3: C, 56.68; H, 3.96; N, 18.36; S, 8.41. Found: C, 56.72; H, 3.92; N, 18.42; S, 8.46. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With acetic acid; In ethanol; at 20℃; for 24h;Inert atmosphere; Reflux; | To 2-hydroxy-4-methoxybenzaldehyde (0.25 g, 0.98 mmol) in 20 mL super dry ethanol <strong>[723-46-6]sulfamethoxazole</strong> (S1) (0.263 g, 0.98 mmol) was added and was stirred at room temperature for 15 min followed by reflux for 24 h. Yellow-orange precipitate appeared and was filtered and washed with ethanol (3 15 mL). The product was dried and crystallized from ethanol at. Yield 72%; mp: 217-219 C. Elemental analysis results (%) for C18H17N3O5S:(Calcd) C, 55.80; H, 4.42; N,10.85; S, 8.28. (Found): C, 55.55; H, 4.20; N, 10.25; S, 8.10. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | General procedure: In a 50 mL flask, Y1-H (1.1mmol), dimethyl formamide (2.0 mL) andfine anhydrous potassium carbonate (1.3mmol) were added. After stirringvigorously 0.5 h, added the compound M5 (0.9mmol). Stirredevenly at room temperature, and monitored the reaction process by TLC.After completion, added saturated brine (15 mL) to the reaction mixture,adjusted pH to 5-6 with 2 mol/L hydrochloric acid in an ice bath, extractedby EtOAc (3×10 mL), combined the organic layer, washed withsaturated brine (15 mL), dried over anhydrous Na2SO4, the crude productwas obtained by drying in vacuo, and the pure TM1 was obtained furtherlyby silica gel column chromatography or recrystallization. 4.2.5.1 TM1a:Methyl (S)-2-(((benzyloxy)carbonyl)amino)-2-(3-(2-((4-(N-(5-methylisoxazol-3-yl)sulfamoyl) phenyl)amino)acetamido)phenyl)acetate Yield 38%, m.p.: 195-197?C, ?+?19.0(c 1.0?mg/mL, Acetone). 1H NMR (DMSO-d6, 300?MHz) delta: 2.3(s, 3H, CH3), 3.63(s, 3H, -COOCH3), 4.49(s, 2H, COCH2), 5.06(s, 2H, ArCH2O), 5.22(d, J?=?7.1?Hz, 1H, CH), 6.25(S, 1H, NH), 6.40(s, 1H, -C=CH-), 6.62(d, J?=?7.9?Hz, 2H, ArH), 7.08(d, J?=?7.4?Hz, 1H, ArH), 7.30-7.36(m, 6H, ArH), 7.51-7.56(m, 4H, ArH), 7.94(s, 1H, -CONH-) 8.21(d, J?=?7.2?Hz, 1H, -CONH-), 10.24(s, 1H, -SO2NH-); 13C NMR (DMSO-d6, 75?MHz) delta: 12.1, 50.2, 52.3, 59.8, 65.7, 96.7, 112.8, 118.4, 118.8, 122.0, 122.8, 128.4, 129.1, 129.4, 136.8, 139.0, 154.0, 155.9, 159.5, 162.3, 165.2, 170.4, 171.1; HR ESI-MS calcd for C29H29N5O8S [M+Na]+630.1624, found 630.1625. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Add to the 1000L glass-lined reactor455kgammonium hydroxide,98kg 3-amino-5-methylisoxazole,At the same time, the steam is heated upThe temperature was raised to 35 to 40 C and stirred for 1 hour.Cool down to 25 ~ 30 C,Then add 260 kg of diphenylureasulfonyl chloride (with temperature rise),Stir and dissolve for 0.5 hours,Cool down to 15 ~ 20 C,Keep warm for 4 hours;After the insulation is over,Add 100kg of 20% sodium hydroxide solution,Adjust PH=14,Warming up to 75-80 C,Reaction for 1 hour;Cool down to below 60 C,Adjust the pH to 5~6 with concentrated hydrochloric acid;Concentrate under reduced pressure to stop heating the total volume of the material about 620kg.At this time, the temperature is about 85 C.Slowly cool down to 8 ~ 10 C,The temperature is controlled to centrifuge at 5 C.The product is dried in a vacuum oven at 70 C to obtain a new product of 240.6 kg.The product content is 99.9%,The product yield was 95.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With acetic acid; In ethanol; at 20℃; for 24.25h;Reflux; | The synthesis method of the Schiff base was depicted schematicallyin Fig. 1b. To 4-(dimethylamino)benzylidene)aminobenzaldehyde (0.15 g, 0.98 mmol) in 20 ml super dry ethanol <strong>[723-46-6]sulfamethoxazole</strong>(0.263 g, 0.98 mmol) was added and was stirred atroom temperature for 15 min followed by reflux for 24 h (Fig. 1).Yellow-orange precipitate appeared and was filtered, washed withethanol (3 15 ml). The product was dried and crystallized fromethanol at. Yield 72%; mp: 218-220 C, APCI-MS (100 eV)m/z:384.13 (M, 100.0%), 385.13 (M+1, 20.9%), 386.12 (M+2, 4.5%).Elemental analysis results (%) for C19H20N4O3S: (Calcd) C, 59.36; H,5.24; N, 14.57; S, 8.34 (Found): C, 59.85; H, 5.21; N, 14.25; S, 8.58. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium carbonate; sodium nitrite; In water; at 0 - 5℃; | The diazotization of <strong>[723-46-6]sulfamethoxazole</strong> (0.5 g,1.97 mmol)(Scheme 1) was carried out at 0-5C in aqueous solution byadding NaNO2 (1.0 g) solution followed by coupling withparacetamol in presence of sodium carbonate (2.0 g) in wateraccording to a general literature procedure18. Bright reddish precipitate filtered and dried at room temperature. It wasthen recrystallized by slow evaporation of hot alcoholic solution and purity was examined by TLC; yield: 85%. Microanalytical data for HL (1): Anal. Calcd. for C18H17N5O5S (Mol.wt. 415): C, 52.04; H, 4.12; N, 16.86%. Found (%): C, 51.95;H, 4.1; N, 16.76; FT-IR bands (KBr pellet, , cm-1) (N=N),1420.47; (C=N), 1616.74; (C=O), 1653.46; (O-H),3364.02; (S-O), 1173.69. [M+] m/z 438. 1H NMR data(DMSO-d6, ppm): 6.188 (4H, s), 9.960 (19N-H, s), 8.141(8,12H, d, J 8.4 Hz), 8.029 (9,11H, d, J 8.4 Hz), 7.038 (15H,d, J 8.7 Hz), 7.605 (16H, d, J 7.2 Hz), 10.590 (5N-H, s),11.627 (14O-H, s), 2.302 (20 -CH3, s), 2.02 (21 -CH3, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.4% | To a stirred solution of sulphonamide (2 mmol),chloroacetylchloride (2 mL) and try ethylamine (0.1 mL)in dry dimethylformamide at 0-5 oC, aminochalcone 1d-1f (2 mmol) was added and stirred at room temperature for3-4 hours by a magnetic stirrer. The stirred reaction mixturewas then refluxed for 8-9 hours. The reaction was monitoredby TLC. After the completion of the reaction, the reactionmixture on hot was poured to crushed ice afforded precipitatesof chalcone-sulphonamide hybrids 3a-6f. Precipitatesthen washed with cold aqueous sodium carbonate and thecrude product was recrystallized in acetone. (E)-2-((4-(3-(2,4-Dihydroxyphenyl)acryloyl)phenyl)amino)-N-(4-(N-(5-methylisoxazol-3-yl)sulfamoyl) phenyl)acetamide(6a): Red solid, mp 121-124 oC Yield 84.4%,Rf 0.62. FT-IR (nu, cm-1): 3741 (-OH), 3672 (-OH), 3649,3568, 3360 (3-NH-), 3064-3100 (Ar C-H), 2974, 2883(Aliphatic-CH), 1734 (-CONH-), 1678 (-CO), 1608 (-C=N),1593 (-HC=CH-), 1454 (C-O), 1396, 1153 (-SO2-) 954 (S-N),831(C-S). 1H NMR (500 MHz, DMSO-d6, ppm): 8.48 (s,1H, -OH), 8.49 (s, 1H, -OH), 7.95 (s, 1H, CONH-), 7.70 (s,1H, -SO2NH-), 7.65 (d, 1Hbeta -CH=CH-), 6.54 (d, 1Halpha-CH=CH-), 6.02-7.93 (m, 10H, Ar-H), 6.01 (t, 1H, -NH-), 3.53(s, 1H, CH=Cisoxazole), 2.88 (d, 2H, -CH2-), 2.73 (s, 3H,-CH3). 13C NMR (500 MHz, DMSO-d6, ppm): 195.17,167.08, 153.09, 151.03, 144.34, 138.80, 130.54, 127.02,126.00, 125.54, 122.95, 119.07, 119.07, 112.40, 40.80, 39.67,39.46, 39.07, 38.83, 30.73, 25.82. HR-MS (ESI) Calculatedfor C27H24N4O7S [M+H+] 548.146, found 548.136. Molecularformula: Calculated C27H24N4O7S, found C27H24N4O7S. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | General procedure: To a stirred solution of sulphonamide (2 mmol),chloroacetylchloride (2 mL) and try ethylamine (0.1 mL)in dry dimethylformamide at 0-5 oC, aminochalcone 1d-1f (2 mmol) was added and stirred at room temperature for3-4 hours by a magnetic stirrer. The stirred reaction mixturewas then refluxed for 8-9 hours. The reaction was monitoredby TLC. After the completion of the reaction, the reactionmixture on hot was poured to crushed ice afforded precipitatesof chalcone-sulphonamide hybrids 3a-6f. Precipitatesthen washed with cold aqueous sodium carbonate and thecrude product was recrystallized in acetone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | General procedure: To a stirred solution of sulphonamide (2 mmol),chloroacetylchloride (2 mL) and try ethylamine (0.1 mL)in dry dimethylformamide at 0-5 oC, aminochalcone 1d-1f (2 mmol) was added and stirred at room temperature for3-4 hours by a magnetic stirrer. The stirred reaction mixturewas then refluxed for 8-9 hours. The reaction was monitoredby TLC. After the completion of the reaction, the reactionmixture on hot was poured to crushed ice afforded precipitatesof chalcone-sulphonamide hybrids 3a-6f. Precipitatesthen washed with cold aqueous sodium carbonate and thecrude product was recrystallized in acetone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With tris(pentafluorophenyl)borate; In N,N-dimethyl-formamide; at 20℃; for 24h;Green chemistry; | Under the air atmosphere,1b (42.3 mg, 0.3 mmol) was sequentially added to the reaction tube.<strong>[723-46-6]Sulfamethoxazole</strong> (50.7 mg, 0.2 mmol),B(C6F5)3 (2.6mg, 0.005mmol),N,N-dimethylformamide (0.5 mL),The reaction system was stirred at room temperature for 24 hours.After the reaction is completed,Dilute with dichloromethane,Remove the solvent,Column chromatography gave a white solid compound 3s (78.7 mg, 86%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h; | To a stirred solution of 4 (500 mg, 1.97 mmol) in diemethylformamide (DMF), dibromoethane 5 (741 mg, 3.94 mmol) and potassium carbonate (682 mg, 4.94 mmol) was added. The mixture was allowed to stir for 1 hr at room temperature. After completion, the mixture was extracted with ethyl acetate two times. The collected organic phase was dried over anhydrous Na2S04, concentrated and purified by column chromatography (9 % EtOAc in Hexane) to obtain 6 (450 mg, 1.25 mmol, 63 % yield) as colorless oil. |
Tags: 723-46-6 synthesis path| 723-46-6 SDS| 723-46-6 COA| 723-46-6 purity| 723-46-6 application| 723-46-6 NMR| 723-46-6 COA| 723-46-6 structure
A596901[ 4563-84-2 ]
Sodium ((4-aminophenyl)sulfonyl)(5-methylisoxazol-3-yl)amide
Reason: Free-salt
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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