Benzyl mercaptan → HCID 19384363, compound

Participants

Reaction Conditions

Reaction Steps

174 g of 2-chloro-3-hydroxybenzaldehyde are dissolved in 1 l of dimethylformamide, 126 ml of benzylmercaptan and 174 g of potassium carbonate are added, and the mixture is stirred for 2 days at 100° C. The reaction mixture is poured into ice-water and extracted using diethyl ether, and the organic phase is washed with saline, dried over sodium sulfate, filtered and concentrated. Silica gel chromatography with ethyl acetate/hexane (1:4) as the mobile phase gives 51.6 g of 2-benzylthio-3-hydroxybenzaldehyde. 31.6 g of this are emulsified in 66 ml of water, and 16.1 g of hydroxylamine-O-sulfonic acid and 1.84 g of sodium sulfate are added. After one hour, 32 ml of each water and methylene chloride are added, and the mixture is treated with 40.4 g of sodium hydrogen carbonate in portions. The reaction mixture is stirred for 2 hours at room temperature and then taken up in methylene chloride, and the organic phase is extracted using 1N potassium hydroxide solution. The aqueous-basic phase is brought to a pH of 1 using concentrated hydrochloric acid and extracted using methylene chloride. The organic phase is dried over sodium sulfate, filtered and concentrated. Recrystallisation from toluene gives 5.93 g of 7-hydroxy-1,2-benzisothiazole of m.p. 185°-187° C.

Provenance & Evidence