Hydrogen Sulfide → HCID 15925276, compound

HRID 704185Notes

Reaction equation

HRID 704185 reaction equation
[ClH:1].[CH3:2][CH:3]1[CH2:7][CH2:6][CH:5]([CH3:8])[N:4]1[CH2:9][CH:10]([N:12]1[C:25]2[CH:24]=[C:23]([C:26](=[S:28])[NH2:27])[CH:22]=[CH:21][C:20]=2[S:19][C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:11].[CH2:29](N)[CH2:30][CH3:31].S>C(O)C>[ClH:1].[CH3:8][CH:5]1[CH2:6][CH2:7][CH:3]([CH3:2])[N:4]1[CH2:9][CH:10]([N:12]1[C:25]2[CH:24]=[C:23]([C:26](=[S:28])[NH:27][CH2:29][CH2:30][CH3:31])[CH:22]=[CH:21][C:20]=2[S:19][C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:11]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 7852PropylamineHCID 20074864HCID 20074864, compound

Product 1

HCID 15925276HCID 15925276, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 10-((2RS)-1-[(2RS,5RS)-2,5-dimethyl-1-pyrrolidinyl]-2-propyl}-2-phenothiazinecarbothioamide hydrochloride (0.9 g) and propylamine (2.9 cc) in absolute ethanol (20 cc) is saturated with hydrogen sulphide and heated for 12 hours to a temperature in the region of 120° C. After cooling, the solution obtained is purged with nitrogen and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is dissolved in ethyl acetate (100 cc) and I the solution is washed with distilled water (2×20 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual yellow oil (1.09 g) is purified by chromatography on a column (height: 30 cm; diameter: 1 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa), eluting with methylene chloride (200 cc) and then with a mixture (95:5 by volume) (250 cc) of methylene chloride and methanol and collecting 50-cc fractions. The combined fractions 3 to 7 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual yellow oil (0.75 g) is dissolved in ethyl acetate (20 cc) and treated with stirring, with a 3N solution (0.6 cc) of hydrochloric acid in ethyl ether. The gum formed is separated by decanting the solvent, taken up in solution in 2-propanol (2 cc) and treated with ethyl ether (10 cc). The solid formed is drained, washed with ethyl ether (2×5 cc) and dried under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C. 10-{(2RS)-1-[(2 RS,5RS)-2,5-Dimethyl-1-pyrrolidinyl]-2-propyl}-N-propyl-2-phenothiazinecarbothioamide hydrochloride (0.63 g) is thereby obtained in the form of a yellow solid, m.p. 138°-140° C. (melts forming a paste).

Workup

  1. temperatureAfter cooling
  2. customthe solution obtained
  3. customis purged with nitrogen
  4. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  5. dissolutionThe residue is dissolved in ethyl acetate (100 cc)
  6. washI the solution is washed with distilled water (2×20 cc)
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  10. customThe residual yellow oil (1.09 g) is purified by chromatography on a column (height: 30 cm; diameter: 1 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa)
  11. washeluting with methylene chloride (200 cc)
  12. customwith a mixture (95:5 by volume) (250 cc) of methylene chloride and methanol and collecting 50-cc fractions
  13. concentrationThe combined fractions 3 to 7 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  14. dissolutionThe residual yellow oil (0.75 g) is dissolved in ethyl acetate (20 cc)
  15. additiontreated
  16. customThe gum formed
  17. customis separated
  18. customby decanting the solvent
  19. additiontreated with ethyl ether (10 cc)
  20. customThe solid formed
  21. washwashed with ethyl ether (2×5 cc)
  22. customdried under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C

Sources & evidence

ORD record
ord-f115db0cbaa2416e8a667817d176207c
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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