Chloroacetyl chloride → HCID 13603691, compound

Participants

Reaction Conditions

Reaction Steps

α-Chloroacetylchloride (13.4 g, 9.5 ml) is added, with exclusion of humidity, under stirring, in 30 minutes, to a solution of the above thiazolidine (12 g) in 1,2-dichloroethane (120 ml) and triethylamine (18 ml), cooled at -10° C. Stirring is continued for 1 hour at 0° C. and the mixture is partitioned with water. The organic phase is separated, washed with water, dried on CaCl2 and the solvents are evaporated to dryness in vacuum. Crystallization from Et2O gives 3-α-chloroacetyl-2-[2'-(o-α-chloroacetoxy-phenyl)ethyl]thiazolidine (12 g), m.p. 88°-89° C. (hexane/AcOEt 7:3, Rf =0.5). A solution of this compound (6 g) in acetone (30 ml) is treated with potassium thioacetate (4.1 g) under stirring for 30 minutes. The mixture is filtered from the inorganic materials, the acetone is evaporated under vacuum and the residue is partitioned between water and EtOAc. From the organic phase after the usual work-up it is obtained 3-acetylthioacetyl-2-[2'-(o-acetylthioacetoxyphenyl)ethyl]thiazolidine as a colourless oil (hexane/AcOEt 7:3, Rf =0.4).

Provenance & Evidence