1-异丙基-2-硫脲

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A suspension of compound 9 (2.1 g, 18 mmol) and 3-bromopyruvic acid (3.0 g, 18 mmol) in dioxane (180 mL) was heated to 80° C. Upon reaching 80° C. the mixture became clear, and soon thereafter the product started to precipitate as a white solid. After 2 h of heating, the reaction mixture was cooled to rt and the precipitate was filtered off and collected. This yielded pure title compound (4.4 g, 94%). Upon reaching 80° C. to precipitate as a white solid After 2 h of heating the reaction mixture was cooled to rt the precipitate was filtered off collected

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Isopropyl-thiourea (2.47 mmol) and 3-(2-Bromo-acetyl)-benzoic acid (2.47 mmol) were mixed in THF (12 mL). After stirring at room temperature for 5 minutes the mixture was heated to 80° C. for 2 hours. The volume was reduced to 5 mL and the mixture was then cooled to −20° C. and filtered. The solid was washed with a small amount of diethylether and dried. m/z=263.1 in MS ES+, which was characterized by hplc and MS and used in the next step without any further purification. was heated to 80° C. for 2 hours the mixture was then cooled to −20° C. filtered The solid was washed with a small amount of diethylether dried used in the next step without any further purification

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Isopropyl-thiourea (2.47 mmol) and 4-(2-Bromo-acetyl)-benzoic acid (2.47 mmol) were mixed in THF (12 mL). After stirring at room temperature for 5 minutes the mixture was heated to 80° C. for 2 hours. The volume was reduced to 5 mL and the mixture was then cooled to −20° C. and filtered. The solid was washed with a small amount of diethylether and dried. m/z=263.1 in MS ES+, which was characterized by hplc and MS and used in the next step without any further purification. was heated to 80° C. for 2 hours the mixture was then cooled to −20° C. filtered The solid was washed with a small amount of diethylether dried used in the next step without any further purification

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A suspension of compound 68 (2.1 g, 18 mmol) and 3-bromopyruvic acid (3.0 g, 18 mmol) in dioxane (180 mL) was heated to 80° C. Upon reaching 80° C. the mixture became clear, and soon thereafter the product started to precipitate as a white solid. After 2 h of heating, the reaction mixture was cooled to rt and the precipitate was filtered off and collected. This yielded pure title product (4.4 g, 94%). Upon reaching 80° C. to precipitate as a white solid After 2 h of heating the reaction mixture was cooled to rt the precipitate was filtered off collected

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Isopropyl thiourea 9 (8.0 g, 67.7 mmol) in 100 ml of dry acetone was added iodomethane (6.3 ml, 101 mmol) dropwise at room temperature. After the addition was completed, the mixture was refluxed for 1 hour, and the solvent was evaporated to dryness under the reduced pressure to give a gum. The gummy hydroiodide salt was suspended in 200 ml of dry methylene chloride and to the suspension was added triethylamine (37.7 ml, 270 mmol). The mixture was stirred for 30 minutes at room temperature, cooled down to −78° C. with a dry ice/acetone bath. To the mixture was added dropwise oxalyl chloride (40.6 ml of 2M solution, 81.2 mmol) and stirred at −78° C. for 1 hour. The reaction was quenched by addition of water to decompose the excess oxalyl chloride, the solvent was dried over Na2SO4 and evaporated to dryness in vacuo. After the addition the mixture was refluxed for 1 hour the solvent was evaporated to dryness under the reduced pressure to give a gum cooled down to −78° C. with a dry ice/acetone bath stirred at −78° C. for 1 hour The reaction was quenched by addition of water the solvent was dried over Na2SO4 evaporated to dryness in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Isopropyl thiourea 9 (8.0 g, 67.7 mmol) in 100 ml of dry acetone was added iodomethane (6.3 ml, 101 mmol) dropwise at room temperature. After the addition was completed, the mixture was refluxed for 1 hour, and the solvent was evaporated to dryness under the reduced pressure to give a gum. The gummy hydroiodide salt was suspended in 200 ml of dry methylene chloride and to the suspension was added triethylamine (37.7 ml, 270 mmol). The mixture was stirred for 30 minutes at room temperature, cooled down to −78° C. with a dry ice/acetone bath. To the mixture was added dropwise oxalyl chloride (40.6 ml of 2M solution, 81.2 mmol) and stirred at −78° C. for 1 hour. The reaction was quenched by addition of water to decompose the excess oxalyl chloride, the solvent was dried over Na2SO4 and evaporated to dryness in vacuo. After the addition the mixture was refluxed for 1 hour the solvent was evaporated to dryness under the reduced pressure to give a gum cooled down to −78° C. with a dry ice/acetone bath stirred at −78° C. for 1 hour The reaction was quenched by addition of water the solvent was dried over Na2SO4 evaporated to dryness in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Isopropyl thiourea 9 (8.0 g, 67.7 mmol) in 100 ml of dry acetone was added iodomethane (6.3 ml, 101 mmol) dropwise at room temperature. After the addition was completed, the mixture was refluxed for 1 hour, and the solvent was evaporated to dryness under the reduced pressure to give a gum. The gummy hydroiodide salt was suspended in 200 ml of dry methylene chloride and to the suspension was added triethylamine (37.7 ml, 270 mmol). The mixture was stirred for 30 minutes at room temperature, cooled down to −78° C. with a dry ice/acetone bath. To the mixture was added dropwise oxalyl chloride (40.6 ml of 2M solution, 81.2 mmol) and stirred at −78° C. for 1 hour. The reaction was quenched by addition of water to decompose the excess oxalyl chloride, the solvent was dried over Na2SO4 and evaporated to dryness in vacuo. After the addition the mixture was refluxed for 1 hour the solvent was evaporated to dryness under the reduced pressure to give a gum cooled down to −78° C. with a dry ice/acetone bath stirred at −78° C. for 1 hour The reaction was quenched by addition of water the solvent was dried over Na2SO4 evaporated to dryness in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The reaction described in Preparation 42 was repeated, but using 3.7 g of isopropylthiourea, 7.4 g of ethyl bromopyruvate and 50 ml of ethanol, giving the title compound as a pale yellow oil. The reaction described in Preparation 42

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 30 g (0.121 mole) of 4,4'-difluorobenzoin, 14.3 g (0.121 mole) of N-isopropylthiourea and 100 ml DMF was heated at reflux through molecular sieves for five hours. The mixture was cooled to room temperature and the crystalline product was collected, washed with DMF/water, then water, then dried to give 22.7 g of 4,5-bis(4-fluorophenyl)-1-isopropylimidazole-2-thiol as a pale yellow solid, mp 308°-312°. was heated at reflux through molecular sieves for five hours the crystalline product was collected washed with DMF/water water, then dried

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A suspension of compound 45 (2.1 g, 18 mmol) and 3-bromopyruvic acid (3.0 g, 18 mmol) in dioxane (180 mL) was heated to 80° C. Upon reaching 80° C. the mixture became clear, and soon thereafter the product started to precipitate as a white solid. After 2 h of heating, the reaction mixture was cooled to rt and the precipitate was filtered off and collected. This yielded pure compound 46 (4.4 g, 94%). Upon reaching 80° C. to precipitate as a white solid After 2 h of heating the reaction mixture was cooled to rt the precipitate was filtered off collected

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A suspension of compound 57 (2.1 g, 18 mmol) and 3-bromopyruvic acid (3.0 g, 18 mmol) in dioxane (180 mL) was heated to 80° C. Upon reaching 80° C. the mixture became clear, and soon thereafter the product started to precipitate as a white solid. After 2 h of heating, the reaction mixture was cooled to rt and the precipitate was filtered off and collected. This yielded pure title compound (4.4 g, 94%). Upon reaching 80° C. to precipitate as a white solid After 2 h of heating the reaction mixture was cooled to rt the precipitate was filtered off collected

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A suspension of compound 9 (2.1 g, 18 mmol) and 3-bromopyruvic acid (3.0 g, 18 mmol) in dioxane (180 mL) was heated to 80° C. Upon reaching 80° C. the mixture became clear, and soon thereafter the product started to precipitate as a white solid. After 2 h of heating, the reaction mixture was cooled to rt and the precipitate was filtered off and collected. This yielded pure title compound (4.4 g, 94%). Upon reaching 80° C. to precipitate as a white solid After 2 h of heating the reaction mixture was cooled to rt the precipitate was filtered off collected