2-phenylethylthiourea

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 13.8 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone is treated with 9.0 g of 1-(phenethyl)-2-thiourea in 150 ml of n-butanol and the mixture is heated to boiling under reflux for 3 hours. After cooling to room temperature, the crystals are filtered under suction and crystallized from n-butanol. There is obtained 3-nitro-5-[2-(phenethylamino)-4-thiazolyl]pyrocatechol hydrobromide of m.p. 249°-251°. the mixture is heated under reflux for 3 hours the crystals are filtered under suction crystallized from n-butanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 13.8 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone is treated with 9.0 g of 1-(phenethyl)-2-thiourea in 150 ml of n-butanol and the mixture is heated to boiling under reflux for 3 hours. After cooling to room temperature, the crystals are filtered under suction and crystallized from n-butanol. There is obtained 3-nitro-5-[2-(phenethylamino)-4-thiazolyl]pyrocatechol hydrobromide of m.p. 249°-251°. the mixture is heated under reflux for 3 hours the crystals are filtered under suction crystallized from n-butanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N-(2-phenylethyl)thiourea (3.60 g, 20 mmol), 2-bromo-1-[4-(trifluoromethyl)phenyl]ethanone (5.34 g, 20 mmol) and N,N-dimethylformamide (5 mL) was stirred at room temperature for 16 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained solid was washed with hexane to give the title compound (5.2 g, yield 74%) as pale-yellow crystals. the mixture was extracted with ethyl acetate The extract was dried over anhydrous sodium sulfate concentrated under reduced pressure The obtained solid was washed with hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromo-1-pyridin-2-ylethanone hydrobromide (4.00 g), N-(2-phenylethyl)thiourea (3.60 g), sodium acetate (1.60 g) and ethanol (30 mL) was stirred with heating under reflux for 1 hr. After cooling, the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio) to give the title compound (2.71 g, yield 48%) as a yellow oil. with heating under reflux for 1 hr After cooling the mixture was extracted with ethyl acetate The ethyl acetate layer was dried over anhydrous magnesium sulfate concentrated The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromo-1-[4-(trifluoromethyl)phenyl]-ethanone (5.34 g), N-(2-phenylethyl)thiourea (3.60 g) and N,N-dimethylformamide (20 mL) was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated to give the title compound (5.20 g, yield 74%) as colorless crystals. extracted with ethyl acetate The ethyl acetate layer was dried over anhydrous magnesium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-pentanone (1.72 g) in methanol (10 mL) was added bromine (3.20 g) at −30° C. The mixture was allowed to warm to room temperature and stirred until the red color of bromine disappeared. To the obtained colorless solution were added sodium acetate (3.20 g) and N-(2-phenylethyl)thiourea (2.70 g) and the mixture was stirred with heating under reflux for 4 hr. A saturated aqueous sodium hydrogencarbonate solution (10 mL) was added to the reaction mixture and the mixture was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio) to give the title compound (850 mg, yield 23%) as pale-yellow crystals. with heating under reflux for 4 hr the mixture was concentrated The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-pentanone (1.72 g) in methanol (10 mL) was added bromine (3.20 g) at −30° C. The mixture was allowed to warm to room temperature and stirred until the red color of bromine disappeared. To the obtained colorless solution were added sodium acetate (3.20 g) and N-(2-phenylethyl)thiourea (2.70 g) and the mixture was stirred with heating under reflux for 4 hr. A saturated aqueous sodium hydrogencarbonate solution (10 mL) was added to the reaction mixture and the mixture was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio) to give the title compound (850 mg, yield 23%) as pale-yellow crystals. with heating under reflux for 4 hr the mixture was concentrated The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-methyl-2-pentanone (2.00 g) in methanol (10 mL) was added bromine (3.20 g) at −30° C. The mixture was allowed to warm to room temperature and stirred until the red color of bromine disappeared. To the obtained colorless solution were added sodium acetate (3.20 g) and N-(2-phenylethyl)thiourea (1.80 g) and the mixture was stirred with heating under reflux for 4 hr. A saturated aqueous sodium hydrogencarbonate solution (10 mL) was added to the reaction mixture and the mixture was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio) to give the title compound (1.15 g, yield 41%) as pale-yellow crystals. with heating under reflux for 4 hr the mixture was concentrated The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-methyl-2-butanone (0.86 g) in methanol (10 mL) was added bromine (1.60 g) at −30° C. The mixture was allowed to warm to room temperature and stirred until the red color of bromine disappeared. To the obtained colorless solution were added sodium acetate (1.60 g) and N-(2-phenylethyl)thiourea (1.80 g) and the mixture was stirred with heating under reflux for 4 hr. A saturated aqueous sodium hydrogencarbonate solution (10 mL) was added to the reaction mixture and the mixture was concentrated. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio) to give the title compound (1.26 g, yield 51%) as colorless crystals. with heating under reflux for 4 hr the mixture was concentrated The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-methyl-2-butanone (0.86 g) in methanol (10 mL) was added bromine (1.60 g) at −30° C. The mixture was allowed to warm to room temperature and stirred until the red color of bromine disappeared. To the obtained colorless solution were added sodium acetate (1.60 g) and N-(2-phenylethyl)thiourea (1.80 g) and the mixture was stirred with heating under reflux for 4 hr. A saturated aqueous sodium hydrogencarbonate solution (10 mL) was added to the reaction mixture and the mixture was concentrated. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio) to give the title compound (1.26 g, yield 51%) as colorless crystals. with heating under reflux for 4 hr the mixture was concentrated The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 13.8 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone is treated with 9.0 g of 1-(phenethyl)-2-thiourea in 150 ml of n-butanol and the mixture is heated to boiling under reflux for 3 hours. After cooling to room temperature, the crystals are filtered under suction and crystallized from n-butanol. There is obtained 3-nitro-5-[2-(phenethylamino)-4-thiazolyl]pyrocatechol hydrobromide of m.p. 249°-251°. the mixture is heated under reflux for 3 hours the crystals are filtered under suction crystallized from n-butanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 13.8 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone is treated with 9.0 g of 1-(phenethyl)-2-thiourea in 150 ml of n-butanol and the mixture is heated to boiling under reflux for 3 hours. After cooling to room temperature, the crystals are filtered under suction and crystallized from n-butanol. There is obtained 3-nitro-5-[2-(phenethylamino)-4-thiazolyl]pyrocatechol hydrobromide of m.p. 249°-251°. the mixture is heated under reflux for 3 hours the crystals are filtered under suction crystallized from n-butanol