Bis-(2-chloroethyl)sulfide → HCID 89812942, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(2-hydroxy-ethylsulfanyl)-ethanol (13.17 g), thionyl chloride (24 mL) in DCM (250 mL) was stirred in an ice/water bath overnight. Then the reaction mixture was concentrated to give crude product 1-chloro-2-(2-chloro-ethylsulfanyl)-ethane (100%), which was used directly in the next step. DBU (42.04 mL) was added slowly to a solution of cyano-acetic acid tert-butyl ester (13.23 g) and 1-chloro-2-(2-chloro-ethylsulfanyl)-ethane (all the crude from previous step) in DMF (200 mL) at rt and then the reaction mixture was stirred in an oil bath (bath temperature=80° C.) overnight. The reaction was cooled, diluted with EtOAc, then washed with cold water, dil. NaCl solution; EtOAc phase was dried over anhydrous sodium sulfate, filtered, concentrated; the residue was column purified to give title compound (7.961 g). 1H NMR in CDCl3, δ in ppm: 3.1-2.9 (m, 2H), 2.7-2.5 (m, 2H), 2.45-2.35 (m, 2H), 2.2-2.1 (m, 2H), 1.51 (s, 9H).

Provenance & Evidence