4-(dimethylamino)butyl carbamimidothioate;dihydrochloride

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

Procedure: A solution of sodium hydroxide (16.4 g) in water (16.5 ml) was added dropwise under nitrogen at 0° C. to a stirred solution of S-[4-(dimethylamino)butyl]-isothiourea dihydrochloride (51 g) in water (60 ml), then the mixture was heated at 95° C. for 2 hours and allowed to cool to ambient temperature. Water (100 ml) was added, and the product was extracted into ether (50 ml), dichloromethane (3×50 ml), and ether (2×50 ml). The combined organic solutions were dried over magnesium sulphate, then the solvents were removed in vacuo. The residue was dissolved in ether and the solution was saturated with hydrogen chloride. The resulting solid was collected by filtration and dried in vacuo at ambient temperature to give 4-(dimethylamino)butanethiol hydrochloride as a white solid (21 g) which was used without further purification. to cool to ambient temperature the product was extracted into ether (50 ml), dichloromethane (3×50 ml), and ether (2×50 ml) The combined organic solutions were dried over magnesium sulphate the solvents were removed in vacuo The residue was dissolved in ether The resulting solid was collected by filtration dried in vacuo at ambient temperature

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

Procedure: A solution of sodium hydroxide (16.4 g) in water (16.5 ml) was added dropwise under nitrogen at 0° C. to a stirred solution of S-[4-(dimethylamino)butyl]-isothiourea dihydrochloride (51 g) in water (60 ml), then the mixture was heated at 95° C. for 2 hours and allowed to cool to ambient temperature. Water (100 ml) was added, and the product was extracted into ether (50 ml), dichloromethane (3×50 ml), and ether (2×50 ml). The combined organic solutions were dried over magnesium sulphate, then the solvents were removed in vacuo. The residue was dissolved in ether and the solution was saturated with hydrogen chloride. The resulting solid was collected by filtration and dried in vacuo at ambient temperature to give 4-(dimethylamino)butanethiol hydrochloride as a white solid (21 g) which was used without further purification. to cool to ambient temperature the product was extracted into ether (50 ml), dichloromethane (3×50 ml), and ether (2×50 ml) The combined organic solutions were dried over magnesium sulphate the solvents were removed in vacuo The residue was dissolved in ether The resulting solid was collected by filtration dried in vacuo at ambient temperature

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

Procedure: A stirred mixture of 1-chloro-4-(dimethylamino)-butane hydrochloride (115 g), thiourea (51.9 g) and ethanol (500 ml) was heated under reflux for 24 hours then allowed to stand at 4° C. for 24 hours. The resulting solid was collected by filtration, washed with ether, and dried in vacuo at ambient temperature for 24 hours to give S-[4-(dimethylamino)butyl]isothiourea dihydrochloride as an off-white solid (140 g), m.p. 179°-182° C. was heated under reflux for 24 hours The resulting solid was collected by filtration washed with ether dried in vacuo at ambient temperature for 24 hours

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

Procedure: A stirred mixture of 1-chloro-4-(dimethylamino)-butane hydrochloride (115 g), thiourea (51.9 g) and ethanol (500 ml) was heated under reflux for 24 hours then allowed to stand at 4° C. for 24 hours. The resulting solid was collected by filtration, washed with ether, and dried in vacuo at ambient temperature for 24 hours to give S-[4-(dimethylamino)butyl]isothiourea dihydrochloride as an off-white solid (140 g), m.p. 179°-182° C. was heated under reflux for 24 hours The resulting solid was collected by filtration washed with ether dried in vacuo at ambient temperature for 24 hours

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

Procedure: A solution of sodium hydroxide (16.4 g) in water (16.5 ml) was added dropwise under nitrogen at 0° C. to a stirred solution of S-[4-(dimethylamino)butyl]-isothiourea dihydrochloride (51 g) in water (60 ml), then the mixture was heated at 95° C. for 2 hours and allowed to cool to ambient temperature. Water (100 ml) was added, and the product was extracted into ether (50 ml), dichloromethane (3×50 ml), and ether (2×50 ml). The combined organic solutions were dried over magnesium sulphate, then the solvents were removed in vacuo. The residue was dissolved in ether and the solution was saturated with hydrogen chloride. The resulting solid was collected by filtration and dried in vacuo at ambient temperature to give 4-(dimethylamino)butanethiol hydrochloride as a white solid (21 g) which was used without further purification. to cool to ambient temperature the product was extracted into ether (50 ml), dichloromethane (3×50 ml), and ether (2×50 ml) The combined organic solutions were dried over magnesium sulphate the solvents were removed in vacuo The residue was dissolved in ether The resulting solid was collected by filtration dried in vacuo at ambient temperature

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

Procedure: A stirred mixture of 1-chloro-4-(dimethylamino)-butane hydrochloride (115 g), thiourea (51.9 g) and ethanol (500 ml) was heated under reflux for 24 hours then allowed to stand at 4° C. for 24 hours. The resulting solid was collected by filtration, washed with ether, and dried in vacuo at ambient temperature for 24 hours to give S-[4-(dimethylamino)butyl]isothiourea dihydrochloride as an off-white solid (140 g), m.p. 179°-182° C. was heated under reflux for 24 hours The resulting solid was collected by filtration washed with ether dried in vacuo at ambient temperature for 24 hours

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

Procedure: A solution of sodium hydroxide (16.4 g) in water (16.5 ml) was added dropwise under nitrogen at 0° C. to a stirred solution of S-[4-(dimethylamino)butyl]-isothiourea dihydrochloride (51 g) in water (60 ml), then the mixture was heated at 95° C. for 2 hours and allowed to cool to ambient temperature. Water (100 ml) was added, and the product was extracted into ether (50 ml), dichloromethane (3×50 ml), and ether (2×50 ml). The combined organic solutions were dried over magnesium sulphate, then the solvents were removed in vacuo. The residue was dissolved in ether and the solution was saturated with hydrogen chloride. The resulting solid was collected by filtration and dried in vacuo at ambient temperature to give 4-(dimethylamino)butanethiol hydrochloride as a white solid (21 g) which was used without further purification. to cool to ambient temperature the product was extracted into ether (50 ml), dichloromethane (3×50 ml), and ether (2×50 ml) The combined organic solutions were dried over magnesium sulphate the solvents were removed in vacuo The residue was dissolved in ether The resulting solid was collected by filtration dried in vacuo at ambient temperature

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

Procedure: A stirred mixture of 1-chloro-4-(dimethylamino)-butane hydrochloride (115 g), thiourea (51.9 g) and ethanol (500 ml) was heated under reflux for 24 hours then allowed to stand at 4° C. for 24 hours. The resulting solid was collected by filtration, washed with ether, and dried in vacuo at ambient temperature for 24 hours to give S-[4-(dimethylamino)butyl]isothiourea dihydrochloride as an off-white solid (140 g), m.p. 179°-182° C. was heated under reflux for 24 hours The resulting solid was collected by filtration washed with ether dried in vacuo at ambient temperature for 24 hours