Aniline → HCID 136332823, compound

Participants

Reaction Steps

5 g (53.7 mmoles) of aniline is dissolved in conc. HCl (13 ml)/water (90 ml) and diazotized with 3.89 g (56.4 mmoles) of sodium nitrite (dissolved in water (8 ml)), at 0-5° C. The resulting solution is slowly added to a solution of 7.52 g (53.7 mmoles) of 4-methylthiophenol in 2N NaOH (54 ml). After stirring overnight the mixture is neutralised with 2N HCl, the precipitate is filtered off, dried, and dissolved in toluene (800 ml). The solution is dried over anhydrous sodium sulfate, filtered through silica gel, and evaporated. Recrystallisation from methanol gives 7.53 g (57%) of dark brown crystals, m.p. 70-80° C.

Provenance & Evidence