Dichloromethane → Ethyl (chlorosulfenyl)(1-methylethyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl (1-methylethyl)carbamate (13.1 g, 0.1 mol) in 100 mlof methylene chloride cooled to 0° C. was added sulfur dichloride (11.3 g, 0.11 mol) in one portion. While maintaining the temperature of the mixture at 0° C., pyridine (8.7 g, 0.11 mol) was added dropwiseover eleven minutes. After complete addition of the pyridine the temperature was allowed to rise to room temperature and stirring was continued for additional 1.5 hours. The mixture was let stand overnight. Methylene chloride was evaporated under vacuum and 100 ml hexane was added. Filteration of pyridine in hydrochloride and evaporation of hexane resulted an orange oil which was distilled in a Kugelrohr apparatus to give 12.5 g of the title Compound B.P.: 64°-80° (bath temp.)

Provenance & Evidence