Hydrogen Sulfide → HCID 15925252, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 10-[(2RS)-1-(N-methyl-N-propylamino)-2-propyl]-2-phenothiazinecarbonitrile (4.3 g) and triethylamine (1.77 cc) in pyridine (86 cc) is treated with hydrogen sulphide and left stirred for 16 hours at a temperature in the region of 20° C. The green solution obtained is diluted with ethyl acetate (200 cc), washed with distilled water (5×40 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual oil (5.4 g) is purified by chromatography on a column (height: 30 cm; diameter: 5.5 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa), eluting with a mixture (97.5:2.5 by volume) (5 liters) of methylene chloride and methanol and collecting 100-cc fractions. The combined fractions 13 to 44 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual yellow oil (4.37 g) is dissolved in ethanol (12 cc) under reflux and treated, with stirring, with a solution of fumaric acid (1.4 g) in ethanol (15 cc) under reflux. After 2 hours, stirring at a temperature in the region of 5° C., the solid formed is drained, washed with ethanol (5 cc) and dried under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C. 10-[(2RS)-1-(N-Methyl-N-propylamino)-2-propyl]-2-phenothiazinecarbothioamide acid fumarate (4.35 g) is thereby obtained in the form of yellow crystals, m.p. 204° C.

Provenance & Evidence