4-Toluenesulfonyl chloride → 1-Chloro-1,4-dicyano-3-thiabutane

Participants

Reaction Steps

To the mixture obtained from Example 1, tosyl chloride (42 g) was added in portions with cooling. The resultant mixture was stirred for 5.5 hours, and then stood overnight. The solution was then poured into 4M hydrochloric acid (300 ml), stirred for 30 minutes, and then extracted with dichloromethane (×4). The combined extracts were washed with saturated brine, dried (magnesium sulphate) and evaporated to obtain the title compound as a dark red oil (30.95 g) 'H n.m.r. δ (CDCl3) 3.35(2H, d, J=7Hz, CH2CH), 3.55(2H,s,CH2CN), 4.77 (1H,t, J=7Hz, CH2CH).

Provenance & Evidence