Carbon Dioxide → Ethyl [(chlorocarbonyl)sulfanyl]acetate

Participants

Reaction Conditions

Reaction Steps

A flask equipped with a refrigerant cooled with dry ice was charged with thioglycolic acid ethyl ester (1.202 g, 10.0 mmol) and triphosgene (2.000 g, 6.7 mmol). A catalytical amount of tetrabutylammonium chloride was added and the mixture was heated to a temperature of 80° C. for fifteen hours. The exhaust gases were treated with 4N sodium hydroxide aqueous solution. The resulting light brown liquid was flushed with a stream of nitrogen, then distilled under vacuum (110° C./4 mbar) to yield the desired compound as a colorless oil. 1H-NMR (400 MHz, CDCl3, reference TMS); δ (ppm): 4.22 (q, 2H), 3.76 (s, 2H), 1.30 (t, 3H). 13C-NMR (100 MHz, CDCl3, reference TMS); δ (ppm): 166.63, 165.05, 62.44, 35.43, 14.02.

Provenance & Evidence