cyclohexylthiourea

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

Procedure: Synthesis was performed from n-cyclohexylthiourea and ethyl 2-bromobutyrate according to Method C. Gave 201 mg (75%). Synthesis Gave 201 mg (75%)

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

Procedure: To a solution of N-(cyclohexylcarbamothioyl)benzamide (17.1 g, 65.5 mmol) in ethanol was added aqueous potassium carbonate (18.2 g, 132.2 mmol). The mixture was stirred at reflux temperature for 4 h. The organic layer was concentrated to a small volume, after which the product could be collected by filtration, then washed with petroleum ether and dried in vacuo to give the title compound as a white solid (9.8 g, 95% two steps). at reflux temperature for 4 h The organic layer was concentrated to a small volume after which the product could be collected by filtration washed with petroleum ether dried in vacuo

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

Procedure: To a solution of N-(cyclohexylcarbamothioyl)benzamide (17.1 g, 65.5 mmol) in ethanol was added aqueous potassium carbonate (18.2 g, 132.2 mmol). The mixture was stirred at reflux temperature for 4 h. The organic layer was concentrated to a small volume, after which the product could be collected by filtration, then washed with petroleum ether and dried in vacuo to give the title compound as a white solid (9.8 g, 95% two steps). at reflux temperature for 4 h The organic layer was concentrated to a small volume after which the product could be collected by filtration washed with petroleum ether dried in vacuo

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

Procedure: Synthesis was performed from n-cyclohexylthiourea and ethyl 2-bromobutyrate according to Method C. Gave 201 mg (75%). Synthesis Gave 201 mg (75%)

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

Procedure: A solution of bromo-(4-oxo-3,4-dihydro-quinazolin-7-yl)acetaldehyde and N-cyclohexylthiourea in dimethylformamide is heated at 70° C. until completion of the reaction (5-12 hours). The mixture is quenched with 10% dimethylamine in ethanol and the solvent is removed under reduced pressured. The crude is purified by chromatography on silica gel to isolate the desired compound. The mixture is quenched with 10% dimethylamine in ethanol the solvent is removed The crude is purified by chromatography on silica gel

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

Procedure: 295.5 g (2.1 mol) of benzoyl chloride were added dropwise over the course of 10 minutes to a solution of 165.0 g (2.2 mol) of ammonium thiocyanate in 500 ml of absolute acetone. After refluxing for 10 minutes, 198.9 g (2.0 mol) of cyclohexylamine were added dropwise, and the mixture was refluxed for a further 20 minutes. It was then stirred into 4 1 of ice-water, and the water was decanted off the oily product. The residue was dissolved in a hot mixture of 2 1 of 10% strength sodium hydroxide solution and 500 ml of ethanol and refluxed for 30 minutes. The reaction mixture was then diluted with ice-water, and the pH was adjusted initially to 1 with concentrated hydrochloric acid and then to 9 with solid sodium bicarbonate. The resulting precipitate was filtered off with suction, washed with water and dried at 80° C. under reduced pressure. After refluxing for 10 minutes the mixture was refluxed for a further 20 minutes the water was decanted off the oily product The residue was dissolved in a hot mixture of 2 1 of 10% strength sodium hydroxide solution and 500 ml of ethanol refluxed for 30 minutes The reaction mixture was then diluted with ice-water The resulting precipitate was filtered off with suction washed with water dried at 80° C. under reduced pressure

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

Procedure: Synthesis was performed from n-cyclohexylthiourea and ethyl 2-bromobutyrate according to Method C. Gave 201 mg (75%). Synthesis Gave 201 mg (75%)

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

Procedure: A solution of bromo-(4-oxo-3,4-dihydro-quinazolin-7-yl)acetaldehyde and N-cyclohexylthiourea in dimethylformamide is heated at 70° C. until completion of the reaction (5-12 hours). The mixture is quenched with 10% dimethylamine in ethanol and the solvent is removed under reduced pressured. The crude is purified by chromatography on silica gel to isolate the desired compound. The mixture is quenched with 10% dimethylamine in ethanol the solvent is removed The crude is purified by chromatography on silica gel

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

Procedure: 295.5 g (2.1 mol) of benzoyl chloride were added dropwise over the course of 10 minutes to a solution of 165.0 g (2.2 mol) of ammonium thiocyanate in 500 ml of absolute acetone. After refluxing for 10 minutes, 198.9 g (2.0 mol) of cyclohexylamine were added dropwise, and the mixture was refluxed for a further 20 minutes. It was then stirred into 4 1 of ice-water, and the water was decanted off the oily product. The residue was dissolved in a hot mixture of 2 1 of 10% strength sodium hydroxide solution and 500 ml of ethanol and refluxed for 30 minutes. The reaction mixture was then diluted with ice-water, and the pH was adjusted initially to 1 with concentrated hydrochloric acid and then to 9 with solid sodium bicarbonate. The resulting precipitate was filtered off with suction, washed with water and dried at 80° C. under reduced pressure. After refluxing for 10 minutes the mixture was refluxed for a further 20 minutes the water was decanted off the oily product The residue was dissolved in a hot mixture of 2 1 of 10% strength sodium hydroxide solution and 500 ml of ethanol refluxed for 30 minutes The reaction mixture was then diluted with ice-water The resulting precipitate was filtered off with suction washed with water dried at 80° C. under reduced pressure

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

Procedure: 5 Grams N-[4-(β-<N'-methyl-N'-pyridyl-ureido>-ethyl)-benzenesulfonyl]-N'-cyclohexyl-thio-urea (prepared by reaction of 4-(β-<N'-methyl-N'-2-pyridyl-ureido>-ethyl)-benzenesulfonamide and cyclohexylisothiocyanate in an acetonic solution in the presence of potassium carbonate, melting point 143°-145° C. from methanol) were dissolved in 50 ml of 1N sodium hydroxide solution. 5 Milliliters of 30% H2O2 were added and the mixture was heated for 15 minutes on the steam bath. After cooling the solution was acidified. The precipitate was suction-filtered and recrystallized from ethanol/dimethylformamide. The N'-[4-(β-<N'-methyl-N'-2-pyridyl-ureido>-ethyl)-benzenesulfonyl]-N'-cyclohexyl-urea obtained melted at 167°-169° C. the mixture was heated for 15 minutes on the steam bath After cooling the solution The precipitate was suction-filtered recrystallized from ethanol/dimethylformamide

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

Procedure: 5 Grams N-[4-(β-<N'-methyl-N'-pyridyl-ureido>-ethyl)-benzenesulfonyl]-N'-cyclohexyl-thio-urea (prepared by reaction of 4-(β-<N'-methyl-N'-2-pyridyl-ureido>-ethyl)-benzenesulfonamide and cyclohexylisothiocyanate in an acetonic solution in the presence of potassium carbonate, melting point 143°-145° C. from methanol) were dissolved in 50 ml of 1N sodium hydroxide solution. 5 Milliliters of 30% H2O2 were added and the mixture was heated for 15 minutes on the steam bath. After cooling the solution was acidified. The precipitate was suction-filtered and recrystallized from ethanol/dimethylformamide. The N'-[4-(β-<N'-methyl-N'-2-pyridyl-ureido>-ethyl)-benzenesulfonyl]-N'-cyclohexyl-urea obtained melted at 167°-169° C. the mixture was heated for 15 minutes on the steam bath After cooling the solution The precipitate was suction-filtered recrystallized from ethanol/dimethylformamide

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

Procedure: 295.5 g (2.1 mol) of benzoyl chloride were added dropwise over the course of 10 minutes to a solution of 165.0 g (2.2 mol) of ammonium thiocyanate in 500 ml of absolute acetone. After refluxing for 10 minutes, 198.9 g (2.0 mol) of cyclohexylamine were added dropwise, and the mixture was refluxed for a further 20 minutes. It was then stirred into 4 1 of ice-water, and the water was decanted off the oily product. The residue was dissolved in a hot mixture of 2 1 of 10% strength sodium hydroxide solution and 500 ml of ethanol and refluxed for 30 minutes. The reaction mixture was then diluted with ice-water, and the pH was adjusted initially to 1 with concentrated hydrochloric acid and then to 9 with solid sodium bicarbonate. The resulting precipitate was filtered off with suction, washed with water and dried at 80° C. under reduced pressure. After refluxing for 10 minutes the mixture was refluxed for a further 20 minutes the water was decanted off the oily product The residue was dissolved in a hot mixture of 2 1 of 10% strength sodium hydroxide solution and 500 ml of ethanol refluxed for 30 minutes The reaction mixture was then diluted with ice-water The resulting precipitate was filtered off with suction washed with water dried at 80° C. under reduced pressure