Thioglycolic Acid → N-(3-Methylphenyl)-2-sulfanylacetamide

Freshly distilled meta-toluidine (10.168 g) was dissolved in toluene (50 ml) and treated with thioglycollic acid (7 ml). The mixture was heated under reflux, and water collected in a Dean and Stark apparatus overnight. The reaction mixture was then cooled and poured into hexane (50 ml). The product separated as an oil and the solvents were removed under reduced pressure to give a white solid (17.975 g). Attempts at recrystallisation resulted in failure and the residue was chromatographed on silica gel. The product (14.84 g), still contaminated with meta toluidine, was taken up in ethyl acetate and washed with 2M hydrochloric acid. The title compound was then isolated in the usual manner as a white solid, yield 13.13 g, mp 58°-60° C.

1. temperatureThe mixture was heated
2. temperatureunder reflux
3. customwater collected in a Dean and Stark apparatus overnight
4. temperatureThe reaction mixture was then cooled
5. additionpoured into hexane (50 ml)
6. customThe product separated as an oil
7. customthe solvents were removed under reduced pressure

ORD record

ord-d4634ae1b3b64909b6921cbe2d457982

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05856273