4-Methylbenzenethiol → HCID 23362221, compound

Participants

Reaction Steps

ρ-Thiocresol (0.43 g) was added slowly to an ice-cooled, stirred suspension of sodium hydride (60% dispersion in oil, 0.14 g) in dry N, N-dimethylformamide (23 mL,) under N2. The mixture was allowed to warm to room temperature over 30 minutes prior to the addition of a solution of methyl 3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-chloropropanoate (1.31 g) in dry N,N-dimethylformamide (16 mL) and the mixture was then left stirring at room temperature for a further 12 hrs. The reaction mixture was diluted with water (375 mL) before extracting with ethyl acetate (3×100 mL). The combined ethyl acetate layers were washed with water (3×100 mL), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel using 60% hexane in ethyl acetate as eluent to afford the title compound which solidified on standing, mp 88.6°-90.1° C.

Provenance & Evidence