Hydrochloric Acid → HCID 22272687, compound

Participants

Reaction Steps

To the resulting nitroaniline (5.80 g, 23.7 mmol) was added concentrated hydrochloric acid (10 ml) with ice cooling and, with stirring, a solution of sodium nitrite (4.27 g, 61.9 mmol) in water (5 ml) was dropped into the resulting suspension during 10 minutes. The mixture was stirred for 1 hour in an ice bath, adjusted to pH, 7 with a saturated aqueous solution of sodium bicarbonate, then sodium thiomethoxide (2.00 g, 28.5 mmol) was added thereto, and the mixture was stirred for 5 minutes. This was stirred at 80° C. for 10 minutes more, the reaction solution was allowed to cool to room temperature, extracted with chloroform, the organic layer was washed with water and a saturated sodium chloride solution successively and dried over anhydrous sodium sulfate and the solvent was evaporated. The residue was purified by a silica gel column chromatography (150 g of silica gel; developing solvent, hexane:benzene=2:1) and the resulting crude crystals were recrystallized from ethyl acetate-hexane to provide 0.87 g (yield 19.8%) of 2-methylthio-6-nitrophenol as pale yellowish brown needles.

Provenance & Evidence