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Structure of 80715-22-6
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CAS No. : | 80715-22-6 |
Formula : | C5H5BrO3 |
M.W : | 193.00 |
SMILES Code : | CC1=C(CBr)OC(=O)O1 |
MDL No. : | MFCD07787463 |
InChI Key : | GWFALVUXAGYMHR-UHFFFAOYSA-N |
Pubchem ID : | 10774141 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H315-H318-H335-H227 |
Precautionary Statements: | P210-P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P332+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501 |
Class: | 8 |
UN#: | 3265 |
Packing Group: | Ⅲ |
* 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 |
---|---|---|
95.4% | With potassium hydrogencarbonate In N,N-dimethyl-formamide at 0℃; for 5 h; Large scale | the reaction vessel in step (3) obtained in prulifloxacin crude acetonitrile and 358L stirred heated to reflux to dissolve transparent, coolish, adding 0. 05kg charcoal, keep stirring under reflux for 30 minutes, filtered hot and the filtrate was natural cooled to room temperature and crystallization, through chilled water cooling crystallization overnight, centrifugation, washing the filter cake with a small amount of acetonitrile frozen crystal, drying, 80 ° C and dried under vacuum to dryness to give prulifloxacin finished 8. 73kg, yield (mole ) 92.4percent, purity 99.5percent 7. 0kg adding the compound of formula (III) in a reaction vessel, 2. 31kg potassium bicarbonate and 42L N, N- dimethylformamide, cooling down to 4 ° C, was added dropwise at a concentration of 0. 6kg / L of formula ( V) DMF solution of compound 12. 3L, controlling the internal temperature 4 ° C, dropwise Bi, 4 ° C with stirring, and the reaction time was 5.5 hours, the reaction solution was poured into ice water with stirring, and stirred for 0.5 hours, the crystals were collected by filtration, the filter cake washed with water until neutral, drained, 60~70 ° C hot air circulation drying, a compound of formula (I) prulifloxacin crude 9. 34kg, yield (moles) 96.8 percent, purity 92.6percent; (4) was added to the reaction vessel in step (3) obtained in prulifloxacin crude acetonitrile and 358L stirred heated to reflux to dissolve transparent, coolish, adding 0. 05kg activated carbon, insulation was stirred at reflux for 30 minutes, filtered hot and the filtrate cooled to room temperature crystallization, crystallization through the chilled water cooling overnight, centrifugation, washing the filter cake with a small amount of acetonitrile frozen crystal, drying, 80 ° C under vacuum to dryness to give Cape Lu Lisha star finished 8. 94kg, yield (mol) of 95.4percent, a purity of 99.7percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.5% | Stage #1: With tert-butylamine hydrobromide; potassium carbonate In acetone at 0 - 55℃; for 32 h; Stage #2: With potassium carbonate; potassium iodide In acetone at 20 - 55℃; for 3 h; |
Ethyl-4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate (100 gm) was dissolved in acetone (2500 ml) and then added potassium carbonate (100 gm), 5-[4'-(bromomethyl)[1,1'-biphenyl]-2-yl]-2-(triphenylmethyl)-1H-tetrazole (250 gm) and tert-butyl ammonium bromide (15 gm) under stirring at room temperature. The temperature of the reaction mass was raised to 50 to 55° C. and maintained for 15 hours at 50 to 55° C. The reaction mass was cooled to 45° C. and passed over celite bed. The collected filtrate was cooled to 0 to 5° C. and then added a solution of potassium carbonate (36 gm) in water (36 ml) for 1 hour. The temperature of the reaction mass was raised to room temperature and maintained for 16 hours at room temperature. The acetone was distilled off completely under vacuum at below 40° C. to obtain residue. To the residue was added sodium chloride solution (10percent, 900 ml) and then added ethyl acetate (1500 ml). The layers were separated and the aqueous layer was extracted. Combined the both organic layers and dried over sodium sulfate. The solvent was distilled off completely to obtain a residual mass. A mixture of acetone (1200 ml), potassium carbonate (100 gm), (4-bromoethyl)-5-methyl-oxo-1,3-dioxane (105 gm) and potassium iodide (17 gm) were added under stirring at room temperature and then the contents were heated to 50 to 55° C. The solution was added to the above residual mass for 1 hour 30 minutes and maintained for 1 hour 30 minutes at 50 to 55° C. The reaction mass was cooled to 45° C. and filtered. The solvent was distilled off completely to obtain residue. Toluene (1500 ml) was added to the residue and the layers were separated. The toluene layer was dried over sodium sulfate and distilled off the layer under vacuum up to obtain clear residual mass. To the residual mass was added methanol (1500 ml) and stirred for 30 minutes at room temperature. The reaction mass was cooled to 10 to 15° C. and maintained for 1 hour 30 minutes. The separated solid was filtered and dried at 40 to 45° C. for 7 hours to obtain 270 gm of trityl olmesartan medoxomil. Trityl olmesartan medoxomil: 98.5percent; Trityl olmesartan ethyl ester impurity: 0.35percent; Bromo trityl olmesartan medoxomil impurity: 0.35percent; Methyl trityl olmesartan medoxomil impurity: 0.34percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.8% | With N-Bromosuccinimide; In chloroform;Reflux; Large scale; | 5. 0kg adding the compound of formula (IV) in a reaction vessel, 8. 0kg N- bromosuccinimide (NBS), 0. 30kg of azobisisobutyronitrile was added as the reaction solvent chloroform 100L, stirring was warmed to 38 ° C, the reaction system to be stable, then slowly heated to reflux for 2-3 hours, the reaction was completed, cooled to room temperature, insolubles were removed by filtration, the filtrate was atmospheric recovery chloroform, 4 ° C refrigerated overnight and filtered again after crystallization the insoluble matter was removed, and then distilled under reduced pressure collecting ll ° C~120 ° C / 5mmHg fractions, the compound of formula (V) 8. 66kg, yield (mole) 938percent, purity 95.1percent.; |
92% | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 77℃; for 6h; | Step III: 4-Bromomethyl-5-methyl~l,3-dioxol~2-one; A mixture of 4,5-dimethyl-l,3-dioxol-2-one (1.5 g, 0.013158 mol), NBS (2.34 g, 0.013158 mol) and benzoyl peroxide (0.089 g, 0.0003684 mol) in CCl4 (20 mL) was stirred at 77°C for 6 hrs (TLC monitoring: cyclohexane/AcOEt 6:4). The solution was treated with an aqueous solution OfNaHCO3 and extracted with CH2Cl2. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to give 4-bromomethyl-5 -methyl- 1,3- dioxol-2-one (2.34 g). Yield: 92percent.1H-NMR (400 MHz, CDCl3, delta): 2.13 (s, 3H, CH3), 4.18 (s, 2H, CH2Br). |
73% | With N-Bromosuccinimide;azobisisobutyronitrile; In tetrachloromethane; | (1) Synthesis of 4-bromomethyl-5-methyl-1,3-dioxolen-2-one[the compound of formula (III) in which X is a bromine atom]: 3.42 g of 4,5-dimethyl-1,3-dioxolen-2-one (synthesised in accordance with Tetrahedron Letters, (1972), pages 1701-1704) was dissolved in 150 ml of carbon tetrachloride, and 5.34 g of N-bromosuccinimide and a catalytic amount of alpha,alpha'-azobisisobutyronitrile were added. The mixture was heated under reflux for 15 minutes. The reaction mixture was concentrated to half of its volume and the resulting insoluble matter was removed by filtration. Concentrating the filtrate gave a syrupy residue. The residue was distilled under reduced pressure to give a fraction boiling at 115° to 120° C./5 mm Hg which was 4.2 g (yield 73percent) of the captioned compound. |
58% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 78℃; for 0.333333h;Darkness; | Example 12: (5-Methyl-2-oxo-l,3-dioxol-4-yl)methyl 4-[(4-methoxyphenyl)amino]-6- (methylcarbamoy^quinoline-S-carboxylate. a) Preparation of the intermed 4-bromomethyl-5-methyl-2-oxo-l,3-dioxolene; To a solution of 4,5-dimethyl-l,3-dioxol-2-one (342 mg, 3.0 mmol) in carbon tetrachloride (10 mL) was added azobisisobutyronitrile (AIBN, 9.8 mg, 0.06 mmol) and iV-bromosuccinimide NBS (580 mg, 3.3 mmol). The reaction mixture was heated in the dark in a stem block at 78 C for 20 minutes. The mixture was cooled and evaporated almost into dryness. The mixture was filtered and the residue was evaporated to give a light yellow solid, which contained 20 percent starting material Yield: 450 mg (58percent). The mixture was used in the next step without further purifi- cation. |
49% | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 2.5h;Heating / reflux; | To a solution of 4,5-dimethyl-1,3-dioxolene-2-one (TCI, 10 g, 88 mmol) and N- bromosuccinimide (Fluka, 15.69 g, 88 mmol) in carbon tetrachloride (250 mL) was added benzoyl peroxide (Acros, 500 mg, 2.1 mmol). The reaction mixture was then refluxed for 2.5 h after which time the volatiles were evaporated under vacuum. The resulting residue was triturated with some carbon tetrachloride, filtered and the solid cake was washed with carbon tetrachloride. The filtrate volatiles were removed under vacuum and the yellow oily residue was distilled under vacuum (2-5 torr) to give 4-bromomethyl-5-methyl-1,3-dioxolene-2-one 903 (8.35 g, b.p. 94-98 °C, 49percent) as a pale yellow oil. 1H NMR (CDCI3) 8 4.21 (s, 2H), 2.17 (s, 3H). |
With N-Bromosuccinimide; azobisisobutyronitrile; In tetrachloromethane; | PREPARATION 18 4-Carbo-(5-methyl-2-oxo-1,3-dioxol-4-ylmethoxy)methylpiperazine hydrochloric acid salt Combine <strong>[37830-90-3]4,5-dimethyl-1,3-dioxol-2-one</strong> (3.42 g, 30 mmol), N-bromosuccinimide (5.34 g, 30 mmol) and AIBN (500 mg, 3 mmol) in anhydrous carbon tetrachloride (100 mL). Heat at reflux. After 2 hours, cool and filter. Concentrate the filtrate to give 4-bromomethyl-5-methyl-1,3-dioxol-2-one (6.5 g, crude) as an oil, which can be used for the next step without further purification. | |
With N-Bromosuccinimide;azobisisobutyronitrile; In tetrachloromethane; | PREPARATION 2 Preparation of 4-bromomethyl-5-methyl-1,3-dioxole-2-one According to the method described in Liebigs. Ann. Chem., 1977, 27-32 4,5-dimethyl-1,3-dioxole-2-one (500 mg, 4.38 mmol) and N-bromosuccinimide (0.78 g, 4.38 mmol) were heated under reflux in dry carbon tetrachloride in the presence of alpha-alpha'-azobisisobutyronitrile (7.5 mg) for 20 minutes. The reaction mixture was concentrated under reduced pressure to half the volume, and the precipitated solid was filtered by suction. After removing the solvent from the filtrate, the residue was analyzed by gas chromatography. The obtained mixture (792 mg), contained 70percent of the desired title compound and used for the subsequent reactions. | |
With N-Bromosuccinimide; In tetrachloromethane; | PREPARATION 1 4-Bromomethyl-5-methyl-2-oxo-1,3-dioxole To a stirred solution of 3.0 g of <strong>[37830-90-3]4,5-dimethyl-2-oxo-1,3-dioxole</strong> in 100 ml of carbon tetrachloride was added 4.63 g of N-bromosuccinimide. The resulting solution was heated under reflux and irradiated for 15 minutes. The reaction mixture was cooled to 0°-5° C., filtered and evaporated to give the title product. The NMR spectrum (CDCl3) showed absorptions at 2.05 (5percent of starting material), 2.18 (3H, s), 4.30 (2H, s) and 4.35 (5percent of dibromo compound) ppm downfield from tetramethylsilane. The IR spectrum showed an absorption at 5.49 microns. | |
With N-Bromosuccinimide;azobisisobutyronitrile; In tetrachloromethane; | (1) 4-Bromomethyl-5-methyl-1,3-dioxolen-2-one [compound of formula (III) in which R is methyl and X is bromine] 3.42 g of 4,5-dimethyl-1,3-dioxolen-2-one [compound of formula (III') in which R is methyl, prepared in accordance with the procedure described in Tetrahedron Letters, pages 1701-1704, (1972)] was dissolved in 150 ml of carbon tetrachloride. To the solution were added 5.34 g of N-bromosuccinimide and a catalytic amount of alpha,alpha'-azobisisobutyronitrile. The mixture was heated under reflux for 15 minutes. The reaction mixture was cooled with ice, and the insoluble materials were removed by filtration. The filtrate was concentrated under reduced pressure to give a syrupy residue. The residue was distilled under reduced pressure, and a fraction having a boiling point of 115° to 120° C./5 mmHg was recovered. Thus, 4.2 g (yield 73percent) of the captioned compound having the following properties was obtained as a colorless liquid. Elemental analysis for C5 H5 BrO3: IR (neat) nu(cm-1): near 18 25 (carbonyl). NMR (CCl4) delta(ppm): 2.10 (3H, --CH3, s), 4.10 (2H, --CH2 Br, s). | |
With N-Bromosuccinimide; In tetrachloromethane; | PREPARATION 1 4-Bromomethyl-5-methyl-2-oxo-1,3-dioxole To a stirred solution of 3.0 g of <strong>[37830-90-3]4,5-dimethyl-2-oxo-1,3-dioxole</strong> in 100 ml of carbon tetrachloride was added 4.63 g of N-bromosuccinimide. The resulting solution was heated under reflux and irradiated for 15 minutes. The reaction mixture was cooled to 0°-5° C., filtered and evaporated to give the title product. The NMR spectrum (CDCl3) showed absorptions at 2.05 (5percent of starting material), 2.18 (3H, s), 4.30 (2H, s) and 4.35 (5percent of dibromo compound) ppm downfield from tetramethylsilane. The infrared spectrum showed an absorption at 5.49 microns. | |
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 2h;Reflux; | A mixture of <strong>[37830-90-3]4,5-dimethyl-1,3-dioxol-2-one</strong> (1.0 g, 8.8 mmol), benzoylperoxide (60 mg, 0.25 mmol) and N-bromosuccinimide (1.6 g, 9.0 mmol) in carbon tetrachloride (10 mL) was heated at reflux for 2 h. The solid was removed from the reaction mixture by filtration. The mother liquid was washed with sat. NaHCO3 and brine, dried over MgSO4 and concentrated. The crude product, 4-(bromomethyl)-5-methyl-1,3-dioxol-2-one, was obtained as a yellow oil (1.7 g) and was used without further purification in the next step. | |
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; for 2h; | To a solution of 16 grams 4,5-dimethyl-1, 3-dioxol-2-one in CC14 (250 mE) was added N135 (23.4 g,131.5 mmol) and AII3N (1.3 g, 7.88 mmol), then the reaction mixture was heated to 80° C. and stirred for 2 hrs. Monitored the starting material gone by TLC. The mixture was filtered and the filtrate was washed with water and brine, the organic phase was dried over Na2504 and concentrated to give crude product as a yellow oil which was used directly next step (25.3 g, yield 93percent). | |
With N-Bromosuccinimide;2,2'-azobis(isobutyronitrile); In tetrachloromethane; | Compound 20 was prepared following the steps disclosed in the literature (Sakamoto er a/., Chem. Pharm. Bull, 1984, 32, 2241). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydrogencarbonate; In N,N-dimethyl-formamide; | EXAMPLE 1 Ethyl 6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4yl)methyl-1-piperazinyl]-4oxo-4H-[1,3-]thiazeto[3,2-a]quinoline-3-carboxylate. Ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate (3.88 g) and 1.23 g of potassium bicarbonate were suspended in 20 ml of N,N-dimethylformamide, 2.38 g of 4-bromomethyl-5-methyl-1,3-dioxolen-2-one was dropped thereinto with ice cooling, and the mixture was stirred for 3 hours. After the reaction, the solvent was evaporated in vacuo therefrom at 50 C. and the residue was extracted with chloroform containing a few amount of methanol. The extract was washed with water, dried, the solvent was evaporated therefrom and the residue was purified by a column chromatography (chloroform-methanol/silica gel) to give 3.32 g of desired product. M.p. 241-243 C. (decompn.) Elem. Anal. for C23 H24 FN3 O6 S; Calcd. (%) C: 56.43 H: 4.94 N: 8.58; Found (%) C: 56.13 H: 4.99 N: 8.26. IR (KBr) nu (cm-1): 1820, 1720 (carbon-yl). NMR (CF3 CO2 D)(ppm) 1.51(3H, COOCH2 CH3, t), 2.31(3H, STR10 s), 2.35(3H, STR11 d), 3.40~4.30(8H, proton in piperazine ring, m), 4.55(2H, STR12 s), 4.65(2H, COOCH2 CH3, q), 6.51(1H, STR13 q), 7.05(1H, 8-proton, d), 8.11(1H, 5-proton, d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2,2'-azobis(isobutyronitrile); In benzene; at 20℃; for 0.5h;Heating / reflux; | (1) 2.08 g of <strong>[37830-90-3]4,5-dimethyl-1,3-dioxol-2-one</strong> was dissolved in 24 mL of benzene, to which 3.25 g of N-bromosuccinimide and 86 mg of 2,2'-azobis(isobutyronitrile) were added at room temperature, and this mixture was stirred for 30 minutes while heating it under reflux. The reaction mixture was cooled to room temperature, and consequently, a solution of 4-bromomethyl-5-methyl-1,3-dioxol-2-one in benzene was obtained.(2) 3.00 g of methyl 3-(5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[3-(methoxymethoxy)-1,2-benzisoxazol-6-yl]methoxy}phenyl) propanoate was dissolved in 15 mL of methanol and 15 mL of tetrahydrofuran, to which a solution of 1.08 g of potassium hydroxide in 4.5 mL of water was added, and this mixture was stirred for one hour at room temperature, and then the solvent was distilled out under reduced pressure. The resultant residue was dissolved in 40 mL of N,N-dimethylformamide, to which 3.60 g of potassium carbonate was added. Then, the benzene solution prepared in (1) was added thereto, and was stirred for one hour at room temperature. The reaction mixture was poured into a mixture of ethyl acetate and water, and adjusted to pH 7 with 6M hydrochloric acid, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous sodium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; toluene:ethyl acetate=5:1] to yield 1.58 g of (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 3-(5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[3-(methoxymethoxy)-1,2-benzisoxazol-6-yl]methoxy}phenyl) propanoate as yellow oil. NMR(400MHz,CDCl3) delta value: 1.5-2.0(8H,m), 2.16(3H,s), 2.75(2H,t,J=7.6Hz), 3.10(2H,t,J=7.6Hz), 3.65(3H,s), 4.5-5.0(3H,m), 5.33(2H,s), 5.57(2H,s), 6.37(1H,dd,J=8.8,2.4Hz), 6.47(1H,d,J=2.4Hz), 6.95(1H,d,J=8.4Hz), 7.35(1H,dd,J=8.4,1.2Hz), 7.4-7.6(4H,m), 7.72(1H,d,J=8.0Hz), 12.67(1H,s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With N-Bromosuccinimide; In tetrachloromethane; | Example 9 Synthesis of 4-bromomethyl-5-methyl-1,3-dioxol-2-one A mixture of <strong>[37830-90-3]4,5-dimethyl-1,3-dioxol-2-one</strong> (15.0 g, 0.132 mol), a,a-azobisisobutyronitrile (AIBN) (1.08 g, 0.0066 mol) and N-bromosuccinimide (23.4 g, 0.132 mol) in freshly distilled carbon tetrachloride (350 mL) was refluxed under nitrogen for 16 h. The mixture was concentrated to one-half the initial volume, cooled in an ice bath and the white solid was filtered off. Concentration of the filtrate (CCl4 solution) in a rotavap under reduced pressure gave 4-bromomethyl-5-methyl-1,3-dioxol-2-one as a pale brown liquid in 90percent yield (25 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With N-Bromosuccinimide; In tetrachloromethane; | 1-bromomethyl-2-methylvinylene carbonate A mixture of <strong>[37830-90-3]dimethylvinylene carbonate</strong> (11.4 g, 100 mmol), N-bromosuccinimide (17.8 g, 100 mmol) and 2,2'-azobisisobutyronitrile (250 mg) in carbon tetrachloride (400 mL) was stirred at reflux for 4 hours. Aqueous workup followed by vacuum distillation (110-112° C., 3.5 mm Hg) gave the desired compound (9.26 g, 48percent). |
With N-Bromosuccinimide; In tetrachloromethane; | EXAMPLE 2 Preparation of 4-bromomethyl-5-methyl-1,3-dioxolene-2-one STR13 4,5-Dimethyl-1,3-dioxolene-2-one (11.4 g) was mixed with N-bromosuccinimide (19.6 g) and 2,2-azobis(2-methylpropionitrile) (0.5 g) in freshly distilled carbon tetrachloride (350 mL) and refluxed for 6 hours under an argon atmosphere. The reaction mixture was cooled in an ice bath after reflux and the precipitate formed was filtered off. The tiltrate was washed with water and brine, and dried over sodium sulfate. The solvent was evaporated to yield a yellow oil (20.54 g) which was distilled to obtain the pure monobromomethyl compound as a light yellow oil (11.86 g, 54percent), bp 93° C. at 0.45 mm; 1 H NMR (CDCl3) delta2.15 (s, 3H), 4.21 (S, 2H); IR (film) 1820, 1728, 1392, 1201, 1236, 768 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 10: Preparation of prulifloxacin hydrochloride; Method A: To the mixture of dimethylformamide (1.5 It) and 6-fluoro-l-methyl-4-oxo-7-(l- piperazinyl)-lH,4H-[l,3]thiazeto[3,2-a]quinoline-3-carboxylic acid (0.3kg), 4-bromomethyl-5- methyl- 1, 3 -dioxolen-2-one, obtained above was added and cooled to 0-50C. Triethylamine (0.87kg) in dimethylformamide (0.3 It) was added slowly in 1-2 hours. After completion of the reaction (monitored by TLC), dichloromethane (3.0 It) and water (1.5 It) were added to the reaction mixture. The layers were separated and aqueous layer was extracted twice with dichloromethane (1.5 It). All organic layers were combined, dried over sodium sulfate followed by distillation. Methanolic hydrochloride (20-25 % w/w, 0.24 It) was added to organic layer at 0- 5C and stirred. The solid, thus precipitated out was filtered, washed with dichloromethane and dried to obtain 0.36kg of the title compound having purity 92.73 % by HPLC. Example 11: Purification of prulifloxacin hydrochlorideDimethylformamide (1.34 It) was added to prulifloxacin hydrochloride (67g) and reaction mass was heated to 110-112C for 1 hour. The reaction mixture was cooled to 25-300C and stirred for 2 hours, filtered, washed with N,iV-dimethylforamide. The product was slurry washed with isopropanol (0.670 It) and dried to obtain 48.8g of title compound having purity 99.30 % by HPLC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77.5% | Into a 250 ml round bottom flask, 5 g of <strong>[147403-52-9]<strong>[147403-52-9]azilsartan</strong> methyl ester</strong> intermediate A4, potassium carbonate 2.2 g, and DMF 70 mL were placed, and the mixture was cooled to -10 to 0 ° C and stirred for 0.5 hour. 2.1 g of 4-bromomethyl-5-methyl-1,3-dioxol-2-one in 30 mL of DMF was added dropwise to the above reaction system. After the addition is completed, the reaction is allowed to rise to room temperature for 2 to 4 hours. After the reaction was completed, 200 mL of water was added, and the pH was adjusted to 2 to 3 with dilute hydrochloric acid, and filtered, and the residue was washed three times with water and then dried.The crude product was purified by silica gel column chromatography.The eluent was dichloromethane-methanol (DCM: MeOH = 50:1).The product was obtained in an amount of 4.8 g, a yield of 77.5percent, and a purity of 97.1percent. |
Tags: 80715-22-6 synthesis path| 80715-22-6 SDS| 80715-22-6 COA| 80715-22-6 purity| 80715-22-6 application| 80715-22-6 NMR| 80715-22-6 COA| 80715-22-6 structure
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Code | Phrase |
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Response | |
Code | Phrase |
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P306 | IF ON CLOTHING: |
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P322 | |
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P378 | |
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P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
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P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
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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 |
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P422 | |
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H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
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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 |
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Health hazards | |
Code | Phrase |
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H305 | May be harmful if swallowed and enters airways |
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H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
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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 |
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H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
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H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
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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 |
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