Hydrogen Sulfide → HCID 14536531, compound

HRID 704180Notes

Reaction equation

HRID 704180 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)-2propyl]-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 cooling, the mixture 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) with a slight excess pressure of nitrogen (40 kPa), eluting successively with methylene chloride (100 cc) and then a 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 cooling
  2. concentrationthe mixture 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) with a slight excess pressure of nitrogen (40 kPa)
  5. washeluting successively with methylene chloride (100 cc)
  6. customa mixture (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-e40004606fe84401a65f4a1d1693d17f
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

Loading…