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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 57684-71-6 |
Formula : | C4H4ClNO |
M.W : | 117.53 |
SMILES Code : | ClCC1=NOC=C1 |
MDL No. : | MFCD06809646 |
InChI Key : | MKFCBJOVMMLPRT-UHFFFAOYSA-N |
Pubchem ID : | 4913025 |
GHS Pictogram: | ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H314 |
Precautionary Statements: | P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 |
Class: | 8 |
UN#: | 3265 |
Packing Group: | Ⅱ |
* 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 |
---|---|---|
78.3% | With hydroxylamine sulfate; In ethanol;Reflux; | Add 400 mL of ethanol to three bottles50.0 g of 1,4-dichloro-3-butenone and 31.0 g of hydroxylamine sulfate.The reaction was heated to reflux and the reaction was monitored by thin layer chromatography.The reaction was poured into 500 mL of ice water, extracted with dichloromethane (100 mL x 3) and the organic phases combined.Washed with saturated sodium bicarbonate, saturated brine, dried over anhydrous sodium sulfate,Under vacuum distillation, 33.1 g (78.3%) of 3-chloromethylisoxazole was collected. |
26 g | With hydroxylamine hydrochloride; In methanol; for 4h;Reflux; | Using chloroacetyl chloride and acetylene gas as raw materials, anhydrous aluminum trichloride as catalyst,Methylene chloride is reacted as a solvent to obtain 1,4-dichloro-3-buten-2-one;Further, 1,4-dichloro-3-buten-2-one and hydroxylamine hydrochloride are refluxed in a methanol solvent to obtain 3-chloromethylisoxazole.The specific step of synthesizing 1,4-dichloro-3-buten-2-one is 110 g, and the chloroacetyl chloride having a molar mass of 1.06 is slowly added dropwise to 150 g.Mixing a mixture of anhydrous AlCl3 having a molar mass of 1.17 and 300 ml of CH2Cl2Cooling to -5 C,The acetylene gas was introduced for 2 hours, the reaction was slowly poured into ice water, and the organic layer was washed with cold water and dried over anhydrous sodium sulfate.The fraction of 78-83 C / 16 mmHg was collected under reduced pressure to give an oil of 64 g of 2,4-dichloro-2-but-2-one.The specific step of synthesizing 3-chloromethylisoxazole is to take 50 g of 2,4-dichloro-2-buten-2-one having a molar mass of 0.36.200 ml of methanol and 25 g of hydroxylamine hydrochloride having a molar mass of 0.36 were heated under reflux for 4 hours, and methanol was distilled off under reduced pressure.The Na2CO3 solution was made alkaline, extracted with ethyl acetate, washed with water, dried over anhydrous Na2SO4.Distillation under reduced pressure gave 26 g of 3-chloromethylisoxazole as an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In ethanol; toluene; acetonitrile; | STR64 A compound of 3-(chloromethyl)-isoxazole (1.2 g) was added dropwise at a temperature of 20 to 30 C. under stirring to a mixture of 7-fluoro-6-(4,5,6,7-tetrahydro-2H-isoindole-1,3-dion-2-yl)-2H-1,4-benzoxazin-3(4H)-one (3.16 g), acetonitrile (50 ml) and potassium carbonate (1.5 g). The reaction mixture was heated under refluxing for 3 hours, cooled to room temperature, and filtered. The filtrate was concentrated under a reduced pressure to dryness. The resultant residue was mixed with toluene (150 ml) to form a suspension, which was then filtered to remove the undissolved materials therefrom. The filtrate was concentrated under a reduced pressure so as to obtain a viscous material, which was thereafter dissolved in a minimum amount of ethanol. The ethanol solution was cooled to precipitate a crystalline product. This product was separated by filtration and dried, so that the aimed compound, i.e. 7-fluoro-4-(isoxazol-3-ylmethyl)-6-(4,5,6,7-tetrahydro-2H-isoindole-1,3-dion-2-yl)-2H-1,4-benzoxazin-3(4H)-one (3.3 g) was obtained. m.p. 206-210 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Thionyl chloride (4.2 ml) was added dropwise to a solution of the product so obtained in chloroform (20 ml) and the mixture was stirred at laboratory temperature for 1 hour. The mixture was evaporated and the crude 3-chloromethylisoxazole so obtained was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ISOPROPYLAMIDE; | The crude product was dissolved in dimethylacetamide (10 ml). Sodium carbonate (approx. 3 g) was added portionwise until the acidity of the reaction mixture was neutralised. Sodium azide (1 equivalent) was added and the mixture was stirred at laboratory temperature for 1.8 hours. The mixture was partitioned between ethyl acetate and water. The organic phase was dried (Na2 SO4) and evaporated. The residue was purified by column chromatography on silica gel using a 1:1 v/v mixture of methylene chloride and hexane as eluent. There was thus obtained 3-azidomethylisoxazole (1.15 g). NMR Spectrum: (CD3 SOCD3) 4.6 (s, 2H), 6.65 (d, 1H), 8.95 (d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triphenylphosphine; In tetrachloromethane; | (b) 3-Chloromethyl isoxazole A solution of 3-hydroxymethyl isoxazole (4.23 g, 43 mmol) and triphenylphosphine (11.3 g, 42 mmol) in carbon tetrachloride (100 ml) was heated at reflux for 18 h. Solvent was removed under reduced pressure then the residue taken up in ether and filtered. The filtrate was concentrated under reduced pressure and further purified by short path distillation (bp 60 C. at 10 mm) to give the desired chloride (1.41 g, 12 mmol, 28%); deltaH (CDCl3) 4.50 (2H, s, CH2 --Cl), 6.40 (1H, d, J 2 Hz, CH-4), 8.40 (1H, d, J 2 Hz, CH-5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethyl phosphite; | (c) 3-Diethylphosphonomethyl isoxazole 3-Chloromethyl isoxazole (1.41 g, 12 mmol) and triethylphosphite (3.13 ml, 18 mmol) were heated at 140 C. for 1 h. Distillation (short path) yielded the phosphonate (390 mg, 1.78 mmol, 15%); bp 110-120 C. at 0.7 mm Hg; deltaH (CDCl3) 1.30 (6H, t, J 7 Hz, OCH2 CH3), 3.30 (2H, d, JP-H 22 Hz, CH2 --P), 4.10 (4H, m, OCH2 CH3), 6.40 (1H, s, CH-4), 8.35 (1H, s, CH-5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
water; In hydrogen bromide; | i. A solution of 3-chloromethylisoxazole (5.8 g) and cysteamine hydrochloride (6.25 g) in aqueous hydrobromic acid (48%, 100 ml) was heated under reflux for 6 hours. Concentration in the presence of water and subsequently n-propanol, followed by recrystallisation of the residue from isopropyl alcohol-ethanol afforded 3-[(2-aminoethyl)-thiomethyl]isoxazole hydrobromide, m.p. 131-133. (Found: Br, 33.6; S, 13.7. C6 H10 N2 OS.HBr requires: Br, 33.4; S, 13.4). | |
water; In hydrogen bromide; | i. A solution of 3-chloromethylisoxazole (5.8 g) and cysteamine hydrochloride (6.25 g) in agueous hydrobromic acid (48%, 100 m1) was heated under reflux for 6 hours. Concentration in the presence of water and subsequently n-propanol, followed by recrystallisation of the residue from isopropyl alcohol-ethanol afforded 3-[(2-aminoethyl)-thiomethyl]isoxazole hydrobromide, m.p. 131-133.(Found: Br, 33.6; S, 13.7. C6 H10 N2 OS.HBr requires: Br, 33.4: S, 13.4). | |
water; In hydrogen bromide; | a. A solution of 3-chloromethylisoxazole (5.8 g.) and cysteamine hydrochloride (6.25 g.) in aqueous hydrobromic acid (48%, 100 ml) was heated under reflux for 6 hours. Concentration in the presence of water and subsequently n-propanol, followed by recrystallisation of the residue from isopropyl alcohol-ethanol afforded 3-[(2-aminoethyl)thiomethyl]isoxazole hydrobromide, m.p. 131-133. (Found: Br, 33.6; S, 13.7. C6 H10 N2 O S. H Br requires: Br, 33.4; S, 13.4). |
water; In hydrogen bromide; | a. A solution of 3-chloromethylisoxazole (5.8 g.) and cysteamine hydrochloride (6.25 g.) in aqueous hydrobromic acid (48%, 100 ml.) was heated under reflux for 6 hours. Concentration in the presence of water and subsequently n-propanol, followed by recrystallisation of the residue from isopropyl alcohol-ethanol afforded 3-[(2-aminoethyl)-thiomethyl]isoxazole hydrobromide, m.p. 131-133. (Found: Br, 33.6; S, 13.7. C6 H10 N2 OS.HBr requires: Br, 33.4; S, 13.4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49.2% | With potassium carbonate; In N,N-dimethyl-formamide; at 55℃; for 18h;Inert atmosphere; | 2-(3-methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(6?-methyl-5?-(trifluoromethyl)-[2,3- bipyridin]-6-yl)acetamide (50 mg, 0.109 mmol) and potassium carbonate (25 mg, 0.327 mmol) were combined in DMF (3 mL) then <strong>[57684-71-6]3-(chloromethyl)isoxazole</strong> (16 mg, 0.120 mmol) was added. The reaction was heated at 55oC for 18 h, cooled to RT then concentrated to a residue which was purified by chromatography eluted with MeOH/DCM (1:99 to 3:97) to give 2-(1-(isoxazol-3- ylmethyl)-3-methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(6?-methyl-5?- (trifluoromethyl)-[2,3?-bipyridin]-6-yl)acetamide (29 mg, 49.2% yield) as a white solid.1H NMR (CDCl3) delta: 9.45 (brd s, 1H), 9.14 (s, 1H), 8.48 (s, 1H), 8.23 (s, 1H), 8.07 (brd s, 1H), 7.82-7.73 (m, 2H), 7.53 (d, J = 8 Hz, 1H), 6.40 (s, 1H), 5.35 (s, 2H), 5.17 (s, 2H) 3.61 (s, 3H), 2.77 (s, 3H). LCMS: MH+ 541 and TR = 3.005 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | To a solution of (S)-2-(3-methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(6'- (trifluoromethyl)-[2,3'-bipyridin]-6-yl)propanamide (15 mg, 0.033 mmol) and POTASSIUM CARBONATE(9 mg, 0.065 mmol) in DMF (1 mL) was added <strong>[57684-71-6]3-(chloromethyl)isoxazole</strong> (3.7 mg, 0.049 mmol). The mixture was stirred at rt overnight. The mixture was diluted with EA and washed with water, saturated aqueous NH4Cl solution and brine, dried over Na2SO4, and evaporated. The residue was purified by silica gel column chromatography (0-2% MeOH/DCM) to give the product (S)-2-(1-(isoxazol-3-ylmethyl)-3-methyl-2,6-dioxo-2,3-dihydro-1H-purin- 7(6H)-yl)-N-(6'-(trifluoromethyl)-[2,3'-bipyridin]-6-yl)propanamide (16.5 mg, 92% yield) as a white solid.1H NMR (400 MHz, DMSO-D6) delta 11.20 (s, 1H), 9.43 (s, 1H), 8.78 (s, 1H), 8.68 (d, J = 1.8 Hz, 1H), 8.39 (s, 1H), 7.89-8.05 (m, 4H), 6.45 (s, 1H), 5.82 (m, 1H), 5.09 (s, 2H), 3.47(s, 3H), 1.87 (d, J = 7.3 Hz, 3H). MH+ 541. |
Tags: 57684-71-6 synthesis path| 57684-71-6 SDS| 57684-71-6 COA| 57684-71-6 purity| 57684-71-6 application| 57684-71-6 NMR| 57684-71-6 COA| 57684-71-6 structure
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