Hydrogen Sulfide → N-[(2RS)-2-Methylbutyl]-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide

HRID 728720Notes

Reaction equation

HRID 728720 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.[CH3:26][CH:27]([CH2:30][CH3:31])[CH2:28]N.S>C(O)C>[CH3:26][CH:27]([CH2:30][CH3:31])[CH2:28][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 72832-MethylbutylamineHCID 14536528HCID 14536528, compound

Product 1

HCID 14536584N-[(2RS)-2-Methylbutyl]-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
115 °C

Procedure

A stirred suspension of 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (2 g) and 2-methylbutylamine (3 cc) in anhydrous ethanol (15 cc) is saturated with hydrogen sulphide and the mixture is heated for 1 hour to a temperature in the region of 115° C. After being cooled, the mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C. The residual yellow paste is taken up with ethyl acetate (30 cc) and distilled water (20 cc). The organic phase is separated, washed with saturated aqueous sodium chloride solution (20 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual viscous yellow oil (2.2 g) is purified by chromatography on a column (height: 40 cm; diameter: 3.2 cm) of silica gel (0.04-0.063 mm), eluting with a mixture (92:8 by volume) (300 cc) of ethyl acetate and methanol and collecting 25-cc fractions. Fractions 6 to 11 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. N-[(2RS)-2-Methylbutyl]-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (1.8 g) is thereby obtained in the form of a viscous yellow oil.

Workup

  1. temperatureAfter being cooled
  2. concentrationthe mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C
  3. distillationdistilled water (20 cc)
  4. customThe organic phase is separated
  5. washwashed with saturated aqueous sodium chloride solution (20 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  9. customThe residual viscous yellow oil (2.2 g) is purified by chromatography on a column (height: 40 cm; diameter: 3.2 cm) of silica gel (0.04-0.063 mm)
  10. washeluting with a mixture (92:8 by volume) (300 cc) of ethyl acetate and methanol
  11. customcollecting 25-cc fractions
  12. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-022907d178a44bdc826dc2e39ef5122c
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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