Methyl Thioglycolate → Methyl-S-(benzamidomethyl)thioglycolate

Participants

Reaction Steps

Methyl thioglycolate (2 g, 18.84 mmol) and chloromethylbenzamide (3.2 g, 18.84 mmol) was dissolved in 60 ml of dry toluene, and the clear solution was stirred for 18 hours at 25° C. under nitrogen at which time a TLC (10% EtOAc/CH2Cl2) showed that the reaction was complete. Solid materials were removed by filtration and the toluene was evaporated to give a pale yellow oil. Purification on silica gel (10% EtOAc/CH2Cl2) yielded a colorless oil that solidified on standing: mp 65°-68° C.; IR (KBr) 3280, 1730, 1620 cm-1 ; NMR (CDCl3) δ7.98-7.25 (m, 5, aryl), 4.77 (d, 2, --SCH2NH--), 3.77 (s, 3, --OCH3), 3.43 (s, 2, --SCH2C=O).

Provenance & Evidence