Hydrogen Sulfide → 10-(1-Diethylamino-2-propyl)-N-propyl-2-phenothiazinecarbothioamide

HRID 704167Notes

Reaction equation

HRID 704167 reaction equation
[CH2:1]([N:3]([CH2:24][CH3:25])[CH2:4][CH:5]([N:7]1[C:20]2[CH:19]=[C:18]([C:21](=[S:23])[NH2:22])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:6])[CH3:2].[CH2:26](N)[CH2:27][CH3:28].S>C(O)C>[CH2:24]([N:3]([CH2:1][CH3:2])[CH2:4][CH:5]([N:7]1[C:20]2[CH:19]=[C:18]([C:21](=[S:23])[NH:22][CH2:26][CH2:27][CH3:28])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:6])[CH3:25]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 7852PropylamineHCID 1453651110-(1-Diethylamino-2-propyl)-2-phenothiazinecarbothioamide

Product 1

HCID 1592524310-(1-Diethylamino-2-propyl)-N-propyl-2-phenothiazinecarbothioamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 10-(1-diethylamino-2-propyl)-2-phenothiazinecarbothioamide acid fumarate, L series (0.56 g) and propylamine (1.4 cc) in absolute ethanol (10 cc) is saturated with hydrogen sulphide and heated for 16 hours to a temperature in the region of 100° C. After cooling, the mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual orange oil is purified by chromatography on a column (height: 25 cm; diameter: 1 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa), eluting with a mixture (80:20 by volume) (150 cc) of ethyl acetate and cyclohexane and collecting 15-cc fractions. The combined fractions 4 to 7 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-(1-Diethylamino-2-propyl)-N-propyl-2-phenothiazinecarbothioamide, L series (0.5 g) is thereby obtained in the form of a yellow oil. 0.25 g of this product is dissolved in isopropyl ether (25 cc) and a 0.3N solution (2.2 cc) of hydrochloric acid in isopropyl ether is added dropwise, with stirring and at a temperature in the region of 5° C. Stirring is maintained for 1 hour at a temperature in the region of 5° C. The precipitate is drained, washed with isopropyl ether (3×5 cc) and dried under reduced pressure (5 mm Hg; 4 kPa) at 40° C. 10-(1-Diethylamino-2-propyl)-N-propyl-2-phenothiazinecarbothioamide hydrochloride, L series (0.24 g) is thereby obtained in the form of a yellow solid, m.p. 95°-100 C. (melts forming a paste), the NMR characteristics of which are identical to those of the product described in Example 6.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  3. customThe residual orange oil is purified by chromatography on a column (height: 25 cm; diameter: 1 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa)
  4. washeluting with a mixture (80:20 by volume) (150 cc) of ethyl acetate and cyclohexane
  5. customcollecting 15-cc fractions
  6. concentrationThe combined fractions 4 to 7 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-de54dc246f184818b2f00889bab13600
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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