Hydrogen Sulfide → HCID 15925266, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 10-{(2RS)-1-[N-methyl-N-(2-hydroxyethyl)amino]-2-propyl}-2-phenothiazinecarbonitrile (3.1 g) and triethylamine (1.3 cc) in anhydrous pyridine (62 cc) is treated with hydrogen sulphide. The greenish solution obtained is then stirred for 16 hours at a temperature in the region of 20° C., purged with nitrogen, poured into distilled water (500 cc) and extracted with ethyl acetate (2×250 cc). The combined organic phases are washed successively with distilled water (2×100 cc) and with saturated aqueous sodium chloride solution (100 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual orange oil (4.8 g) is purified by chromatography on a column (height: 30 cm, diameter: 2.8 cm) of silica gel (0.2-0.063 mm), eluting with a mixture (75:25 by volume) (3 liters) of ethyl acetate and cyclohexane and collecting 50-cc fractions. The combined fractions 19 to 50 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-{(2RS)-1-[N-methyl-N-(2-hydroxyethyl)amino]-2-propyl}-2-phenothiazinecarbothioamide (2.2 g) is thereby obtained in the form of a yellow product of meringue-like consistency.

Provenance & Evidence