Hydrogen Sulfide → HCID 14536602, compound

Participants

Reaction Steps

A solution of 10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide, L series (6 g) and 3-methylbutylamine (18.9 cc) in absolute ethanol (90 cc) is saturated with hydrogen sulphide and brought for 16 hour to a temperature in the region of 105° C. After cooling, the reaction mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The oily brown residue is purified by chromatography on a column (height: 40 cm; diameter: 4 cm) of silica gel (0.02-0.063 mm), eluting with methylene chloride (1 liter) and then with a mixture (95:5 by volume) (1.5 liters) of methylene chloride and methanol and collecting 80-cc fractions. Fractions 23 to 36 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. N-(3-Methylbutyl)-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide, L series (6.76 g) is thereby obtained in the form of an orange oil. 1 g of this oil is dissolved in ethyl acetate (10 cc), and a 3.3N solution (0.7 cc) of hydrochloric acid in isopropyl ether is introduced with stirring. After 30 minutes' stirring at a temperature in the region of 5° C., the crystals formed are drained, washed with diethyl ether (3×10 cc) and dried under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C. N-(3-Methylbutyl)-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide hydrochloride, L series (0.75 g) is thereby obtained in the form of yellow crystals, m.p. 186° C., the NMR spectrum of which is identical to that of the product obtained in Example 35.

Provenance & Evidence