Chloroacetic Acid → HCID 18625228, compound

Participants

Reaction Steps

To a mixture of 174.15 g (0.50 mol) of N,N-di-n-butyl-N′-(4-t-butylbenzoyl)thiourea (compound 1-2), 44.0 g (1.10 mol) of sodium hydroxide and 500 ml of water was added 56.70 g (0.60 mol) of chloroacetic acid. The mixture was stirred and heated on a steam bath for 22 hrs and cooled. The water phase was decanted from the solid phase, and the solid was washed with water and methanol. Recrystallization of the solid from methanol gave 85.6 g (49.7% yield) of product; mp: 48.5-49.5° C. The NMR spectrum was consistent with the proposed structure. Anal. Calcd. for C21H32N2S: C, 73.20; H, 9.36; N, 8.13; S, 9.30. Found: C, 73.04; H, 9.29; N, 8.02; S, 9.19.

Provenance & Evidence