Hydrogen Sulfide → HCID 14536624, compound

HRID 704204Notes

Reaction equation

HRID 704204 reaction equation
[N:1]1([CH2:6][CH:7]([N:9]2[C:22]3[CH:21]=[C:20]([C:23](=[S:25])[NH2:24])[CH:19]=[CH:18][C:17]=3[S:16][C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH3:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:26].[CH3:27][CH:28]([CH3:33])[CH2:29][CH2:30][CH2:31]N.S>C(O)C>[ClH:26].[CH3:27][CH:28]([CH3:33])[CH2:29][CH2:30][CH2:31][NH:24][C:23]([C:20]1[CH:19]=[CH:18][C:17]2[S:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH:7]([CH3:8])[CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:22]=2[CH:21]=1)=[S:25]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 126557894-methylpentan-1-amine hydrochlorideHCID 1453652810-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide

Product 1

HCID 14536624HCID 14536624, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (2 g) and 4-methylpentylamine hydrochloride (7.4 g) is absolute ethanol (30 cc) is saturated with hydrogen sulphide. The reaction mixture is then brought for 16 hours to a temperature in the region of 105° C. After cooling, the mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The pasty residue (5 g) is purified by chromatography on a column (height: 35 cm; diameter: 3 cm) of silica gel (0.2-0.063 mm), eluting successively with methylene chloride (500 cc) and then with a mixture (95:5 by volume) (500 cc) of methylene chloride and methanol, collecting 30-cc fractions. Fractions 25 to 28 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual orange oil (2.16 g) is dissolved in ethyl acetate (10 cc), and a 3.3N solution (1.5 cc) of hydrochloric acid in isopropyl ether is added with stirring, followed by ethyl ether until a persistent cloudiness has formed. After 1 hour at a temperature in the region of 5° C., the solid formed is drained, washed with ethyl ether (3×10 cc) and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C. N-(4-Methylpentyl)-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide hydrochloride (1.7 g) is thereby obtained in the form of a yellow solid, m.p. 186° C.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  3. customThe pasty residue (5 g) is purified by chromatography on a column (height: 35 cm; diameter: 3 cm) of silica gel (0.2-0.063 mm)
  4. washeluting successively with methylene chloride (500 cc)
  5. customwith a mixture (95:5 by volume) (500 cc) of methylene chloride and methanol, collecting 30-cc fractions
  6. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  7. dissolutionThe residual orange oil (2.16 g) is dissolved in ethyl acetate (10 cc)
  8. additiona 3.3N solution (1.5 cc) of hydrochloric acid in isopropyl ether is added
  9. customhas formed
  10. waitAfter 1 hour at a temperature in the region of 5° C.
  11. customthe solid formed
  12. washwashed with ethyl ether (3×10 cc)
  13. customdried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C

Sources & evidence

ORD record
ord-0d662a3754eb40b99072c29354a4ebe9
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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