Ethanethiol → Carbonothioic acid, O-(1-chloroethyl) S-ethyl ester

A solution of 1-chloroethyl chloroformate (71.5 g, 0.5 mol) in diethyl ether (600 mL) was cooled to 0-4° C. in an ice-water bath and a solution of ethanethiol (37 mL, 0.5 mol) and triethylamine (69.3 mL, 0.5 mol) in diethyl ether (200 mL) was added dropwise over 1 h. The reaction mixture was removed from the ice bath and stirred at ambient temperature for 4 h. Triethylamine hydrochloride was removed by filtration, the filtrate concentrated under reduced pressure and the residue purified by vacuum distillation (67-68° C. at 240 mTorr) to afford the title compound (2) as a colorless liquid (75 g, 89%). 1H NMR (CDCl3, 400 MHz): δ 1.35 (t, 3H), 1.8 (d, 3H), 2.9 (dq, 2H), 6.6 (q, 1H).

1. customThe reaction mixture was removed from the ice bath
2. customTriethylamine hydrochloride was removed by filtration
3. concentrationthe filtrate concentrated under reduced pressure
4. distillationthe residue purified by vacuum distillation (67-68° C. at 240 mTorr)

ORD record

ord-4b9b6301407645a58c102b5f0a106557

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07511158B2