N-cyclohexylsulfamoyl chloride

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Triethylamine (112 g) is added to a stirred solution of N-carbomethoxy-O-methylisourea (132.1 g) in anhydrous THF (900 ml). The solution is cooled to -70° C. under an N2 atmosphere and solution of cyclohexylsulfamoyl chloride (198 g) in anhydrous THF (400 ml) is added dropwise to the reaction mixture. The reaction mixture is warmed to RT filtered through Celite®, washed with anhydrous THF and evaporated to yield an oil which is taken up in methylene chloride, washed with 0.5N HCl and allowed to stand overnight. The organic layer is washed with 0.5N HCl, dried, filtered, washed with methylene chloride, evaporated and dried under high vacuum affording the desired product as an oil which is used in the next step without further purification. The reaction mixture is warmed to RT filtered through Celite® washed with anhydrous THF evaporated to yield an oil which washed with 0.5N HCl The organic layer is washed with 0.5N HCl dried filtered washed with methylene chloride evaporated dried under high vacuum

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Triethylamine (112 g) is added to a stirred solution of N-carbomethoxy-O-methylisourea (132.1 g) in anhydrous THF (900 ml). The solution is cooled to -70° C. under an N2 atmosphere and solution of cyclohexylsulfamoyl chloride (198 g) in anhydrous THF (400 ml) is added dropwise to the reaction mixture. The reaction mixture is warmed to RT filtered through Celite®, washed with anhydrous THF and evaporated to yield an oil which is taken up in methylene chloride, washed with 0.5N HCl and allowed to stand overnight. The organic layer is washed with 0.5N HCl, dried, filtered, washed with methylene chloride, evaporated and dried under high vacuum affording the desired product as an oil which is used in the next step without further purification. The reaction mixture is warmed to RT filtered through Celite® washed with anhydrous THF evaporated to yield an oil which washed with 0.5N HCl The organic layer is washed with 0.5N HCl dried filtered washed with methylene chloride evaporated dried under high vacuum

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

Procedure: To a solution of cyclohexylsulfamic acid (5 g, 27.9 mmol) in benzene (30 mL) was added dropwise phosphorus pentachloride (6.4 g, 30.7 mmol), and the mixture heated at reflux for 4 h. After the solvent was removed, the residue was distilled under reduced pressure to give the title compound (5 g, 91%). the mixture heated at reflux for 4 h After the solvent was removed the residue was distilled under reduced pressure

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

Procedure: To a solution of cyclohexylsulfamic acid (5 g, 27.9 mmol) in benzene (30 mL) was added dropwise phosphorus pentachloride (6.4 g, 30.7 mmol), and the mixture heated at reflux for 4 h. After the solvent was removed, the residue was distilled under reduced pressure to give the title compound (5 g, 91%). the mixture heated at reflux for 4 h After the solvent was removed the residue was distilled under reduced pressure

Conditions: temp:83.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 15 parts of dimethylcarbamic acid chloride in 310 parts of 1,2-dichloroethane is saturated with 30 parts of phosgene at 25° C and 89.5 parts of cyclohexylsulfamic acid are then added. The reaction mixture is heated to 83° C whilst continuing to introduce phosgene. In total, 330 parts of phosgene are introduced in the course of 13 hours. After removing the solvent and the dimethylcarbamic acid chloride under reduced pressure, the residue is distilled, and 57 parts (58% of theory) of cyclohexylsulfamic acid chloride of boiling point 208°-127° C/0.1 mm Hg and melting point 42°-44° C are obtained. After removing the solvent the dimethylcarbamic acid chloride under reduced pressure, the residue is distilled

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

Procedure: 15 parts of dichloromethylenedimethylammonium chloride, suspended in 540 parts of 1,2-dichloroethane, are saturated with 40 parts of phosgene at 35° C, whilst stirring. 89.6 parts of cyclohexylsulfamic acid are now added and a further 550 parts of phosgene are then introduced in the course of 15 hours at 83° C, whilst stirring. After removing excess phosgene, and the solvent, under reduced pressure, 67.2 parts (68% of theory) of cyclohexylsulfamic acid chloride of boiling point 100°-114° C/0.01 mm Hg and melting point 43°-47° C are obtained by distillation of the residue. whilst stirring After removing excess phosgene

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

Procedure: 15 parts of dichloromethylenedimethylammonium chloride, suspended in 540 parts of 1,2-dichloroethane, are saturated with 40 parts of phosgene at 35° C, whilst stirring. 89.6 parts of cyclohexylsulfamic acid are now added and a further 550 parts of phosgene are then introduced in the course of 15 hours at 83° C, whilst stirring. After removing excess phosgene, and the solvent, under reduced pressure, 67.2 parts (68% of theory) of cyclohexylsulfamic acid chloride of boiling point 100°-114° C/0.01 mm Hg and melting point 43°-47° C are obtained by distillation of the residue. whilst stirring After removing excess phosgene

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 13.6 g of the cyclohexylsulfamoyl chloride (69 mmol) in 100 mL of dichloromethane is added under argon atmosphere to a solution of 1-hexadecylamine (19.9 g, 82 mmol) and triethylamine (47.5 mL, 340 mmol) in 300 mL of dichloromethane. The reaction mixture is stirred 5 hours at 0° C., neutralized with an aqueous Na2CO3 solution and concentrated under reduced pressure. The residue is taken up in dichloromethane (800 mL). The organic components are successively washed with diluted hydrochloric aqueous solution, NaHCO3 aqueous solution and brine, dried (Na2SO4), and concentrated under reduced pressure. The residue is suspended in ether, filtered through Büchner, and the precipitate is washed two times with 100 ml of ether to yield a white powder of N-cyclohexyl-N′-hexadecylsulfamide (21.8 g, 79%). concentrated under reduced pressure The organic components are successively washed with diluted hydrochloric aqueous solution, NaHCO3 aqueous solution and brine dried (Na2SO4) concentrated under reduced pressure filtered through Büchner the precipitate is washed two times with 100 ml of ether

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 13.6 g of the cyclohexylsulfamoyl chloride (69 mmol) in 100 mL of dichloromethane is added under argon atmosphere to a solution of 1-hexadecylamine (19.9 g, 82 mmol) and triethylamine (47.5 mL, 340 mmol) in 300 mL of dichloromethane. The reaction mixture is stirred 5 hours at 0° C., neutralized with an aqueous Na2CO3 solution and concentrated under reduced pressure. The residue is taken up in dichloromethane (800 mL). The organic components are successively washed with diluted hydrochloric aqueous solution, NaHCO3 aqueous solution and brine, dried (Na2SO4), and concentrated under reduced pressure. The residue is suspended in ether, filtered through Büchner, and the precipitate is washed two times with 100 ml of ether to yield a white powder of N-cyclohexyl-N′-hexadecylsulfamide (21.8 g, 79%). concentrated under reduced pressure The organic components are successively washed with diluted hydrochloric aqueous solution, NaHCO3 aqueous solution and brine dried (Na2SO4) concentrated under reduced pressure filtered through Büchner the precipitate is washed two times with 100 ml of ether

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

Procedure: Under a nitrogen atmosphere, a solution of N-cyclohexylsulfamic acid (50 g, 279 mmol) and PCl5 (58.1 g, 279 mmol) in 150 mL of toluene is very gently warmed up to 100° C. and maintained at that temperature for 1 hour. Distillation of the solution yields N-cyclohexylsulfamoyl chloride as a colorless solid (45.5 g, 82%). maintained at that temperature for 1 hour Distillation of the solution

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Triethylamine (112 g) is added to a stirred solution of N-carbomethoxy-O-methylisourea (132.1 g) in anhydrous THF (900 ml). The solution is cooled to -70° C. under an N2 atmosphere and solution of cyclohexylsulfamoyl chloride (198 g) in anhydrous THF (400 ml) is added dropwise to the reaction mixture. The reaction mixture is warmed to RT filtered through Celite®, washed with anhydrous THF and evaporated to yield an oil which is taken up in methylene chloride, washed with 0.5N HCl and allowed to stand overnight. The organic layer is washed with 0.5N HCl, dried, filtered, washed with methylene chloride, evaporated and dried under high vacuum affording the desired product as an oil which is used in the next step without further purification. The reaction mixture is warmed to RT filtered through Celite® washed with anhydrous THF evaporated to yield an oil which washed with 0.5N HCl The organic layer is washed with 0.5N HCl dried filtered washed with methylene chloride evaporated dried under high vacuum

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 54.2 parts of phosphorus pentachloride are added in portions to 89.6 parts of cyclohexylsulfamic acid, suspended in a mixture of 113 parts of 1,2-dichloroethane and 134 parts of phosphorus oxychloride, at 20° C, whilst stirring. The reaction mixture is then heated to 95° C in the course of 30 minutes and is stirred at from 95° to 98° C for 71/2 hours. After removing the solvent under reduced pressure distillation of the residue gives 94 parts (95% of theory) of cyclohexylsulfamic acid chloride of boiling point 103°-111° C/0.05 mm Hg (melting point 42°-44°). is stirred at from 95° to 98° C for 71/2 hours After removing the solvent under reduced pressure distillation of the residue