Dicyclohexylcarbodiimide → S-(4-Fluorobenzyl) 3-benzylthiopropionothioate

Reaction equation

C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([CH2:23][CH2:24][C:25](O)=[S:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][SH:34])=[CH:31][CH:30]=1>C(Cl)Cl>[CH2:16]([CH2:23][CH2:24][C:25](=[S:26])[S:34][CH2:33][C:32]1[CH:35]=[CH:36][C:29]([F:28])=[CH:30][CH:31]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Procedure

6.18 g (30 mmoles) of dicyclohexylcarbodiimide in 20 ml of methylene chloride were added to a solution, which had been cooled to 0° C., of 5.9 g (30 mmoles) of 3-benzylthiopropionic acid and 4.26 g (30 mmoles) of 4-fluorobenzylmercaptan in 25 ml of methylene chloride, and the mixture was kept overnight at room temperature. After filtering off the dicyclohexylurea and stripping off the solvent, the crude product was purified, first by chromatography, on silica gel, from 1:2 methylene chloride/petroleum ether and then by distillation in a bulb tube.