Hydrogen Sulfide → HCID 14536579, compound

HRID 728718Notes

Reaction equation

HRID 728718 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][CH2:28][CH2:29][CH3:30].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][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8060PentylamineHCID 1453652810-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide

Product 1

HCID 14536579HCID 14536579, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (2 g and pentylamine (3 cc) in absolute ethanol (30 cc) is saturated with hydrogen sulphide and then heated for 2 hours to a temperature in the region of 100° C. After being cooled, the mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The pasty residue is taken up with ethyl ether (50 cc) and distilled water (15 cc). The organic phase is separated, dried over potassium carbonate and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual viscous yellow oil is purified by chromatography on a column (height: 35 cm; diameter: 2.6 cm) of silica gel (0.2-0.063 mm), eluting with ethyl acetate (300 cc) and collecting 25-cc fractions Fractions 3 to 9 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. N-Pentyl-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (2.25 g) is thereby obtained in the form of a yellow oil.

Workup

  1. temperatureAfter being cooled
  2. concentrationthe mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  3. distillationdistilled water (15 cc)
  4. customThe organic phase is separated
  5. dry with materialdried over potassium carbonate
  6. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  7. customThe residual viscous yellow oil is purified by chromatography on a column (height: 35 cm; diameter: 2.6 cm) of silica gel (0.2-0.063 mm)
  8. washeluting with ethyl acetate (300 cc)
  9. customcollecting 25-cc fractions Fractions 3 to 9
  10. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-bc82ee6b1c164e498adf6957ff3533d9
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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