Hydrogen Sulfide → HCID 14536531, compound

HRID 728702Notes

Reaction equation

HRID 728702 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.[CH2:26](N)[CH2:27][CH3:28].S>C(O)C>[CH2:26]([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])[CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 7852PropylamineHCID 1453652810-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide

Product 1

HCID 14536531HCID 14536531, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (0.9 g) and propylamine (3 cc) in absolute ethanol (18 cc) is saturated with hydrogen sulphide and the mixture is brought to a temperature in the region of 100° C. for 16 hours. After being cooled, it is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to obtain a yellow oil. This oil is purified by chromatography on a column (height: 25 cm; diameter: 2.5 cm) of silica gel (0.04-0.063 mm) under a slight excess pressure of nitrogen (40 kPa), eluting successively with methylene chloride (100 cc) and then mixture (95:5 by volume) (300 cc) of methylene chloride and methanol and collecting 50-cc fractions. Fractions 3 to 5 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual yellow oil (1 g) is dissolved in ethanol (9 cc) under reflux and treated with a.boiling solution of fumaric acid (0.29 g) in ethanol (5 cc). The mixture is allowed to cool and is maintained for 4 hours at a temperature in the region of 5° C. The crystals formed are drained, washed with ice-cold ethanol (2 cc) and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 35° C. N-Propyl-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide neutral fumarate (1.12 g) is thereby obtained in the form of yellow crystals, m.p. 150-152° C.

Workup

  1. temperatureAfter being cooled
  2. concentrationit is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  3. customto obtain a yellow oil
  4. customThis oil is purified by chromatography on a column (height: 25 cm; diameter: 2.5 cm) of silica gel (0.04-0.063 mm) under a slight excess pressure of nitrogen (40 kPa)
  5. washeluting successively with methylene chloride (100 cc)
  6. custommixture (95:5 by volume) (300 cc) of methylene chloride and methanol and collecting 50-cc fractions
  7. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  8. dissolutionThe residual yellow oil (1 g) is dissolved in ethanol (9 cc)
  9. temperatureunder reflux
  10. additiontreated with a.boiling solution of fumaric acid (0.29 g) in ethanol (5 cc)
  11. temperatureto cool
  12. customThe crystals formed
  13. washwashed with ice-cold ethanol (2 cc)
  14. customdried under reduced pressure (5 mm Hg; 0.7 kPa) at 35° C

Sources & evidence

ORD record
ord-9c066eafd56a46c5a5246cda3c32393d
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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