Hydrogen Sulfide → HCID 14536542, compound

HRID 728706Notes

Reaction equation

HRID 728706 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].N1(CC([C:15]2[C:28]3[NH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[S:20][C:19]=3[CH:18]=[CH:17][C:16]=2[C:29](=[S:31])[NH2:30])C)CCCCCC1.S>C(O)C>[N:4]1([CH2:17][CH:18]([N:27]2[C:28]3[CH:15]=[C:16]([C:29](=[S:31])[NH:30][CH2:22][CH2:21][CH3:26])[CH:17]=[CH:18][C:19]=3[S:20][C:21]3[C:26]2=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:19])[CH2:28][CH2:15][CH2:16][CH2:3][CH2:2][CH2:1]1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 7852PropylamineHCID 86745075HCID 86745075, compound

Product 1

HCID 14536542HCID 14536542, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

n-Propylamine (3.3 cc) is added to a solution of -[(2RS)-1-(perhydro-1-azepinyl)-2-propyl]-2-phenothiazinecarbothioamide (3.2 g) in absolute ethanol (80 cc). The mixture is saturated with hydrogen sulphide and then brought to 150° C. for 16 hours. The reaction mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa). The residue is diluted with ethyl 5 acetate (150 cc), washed with distilled water (3×100 cc) and with saturated sodium chloride solution (100 cc), dried over magnesium sulphate and then concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) before being purified by chromatography on a column (height: 32 cm; diameter: 4 cm) of silica gel (0.06-0.2 mm), eluting with a 60:40 (by volume) mixture (1,000 cc) of cyclohexane and ethyl acetate, collecting 60-cc fractions. Fractions 3 to 11 are combined and concentrated to dryness at 50° C. under reduced pressure (30 mm Hg; 4 kPa) to give 10-[(2RS)-1-(perhydro-1-azepinyl)-2-propyl]-N-propyl-2-phenothiazinethiocarboxamide (2.5 g) in the form of a clear orange oil.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa)
  2. additionThe residue is diluted with ethyl 5 acetate (150 cc)
  3. washwashed with distilled water (3×100 cc) and with saturated sodium chloride solution (100 cc)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa)
  6. custombefore being purified by chromatography on a column (height: 32 cm; diameter: 4 cm) of silica gel (0.06-0.2 mm)
  7. washeluting with a 60:40 (by volume) mixture (1,000 cc) of cyclohexane and ethyl acetate
  8. customcollecting 60-cc fractions
  9. concentrationconcentrated to dryness at 50° C. under reduced pressure (30 mm Hg; 4 kPa)

Sources & evidence

ORD record
ord-a9a192d73e0e4469ac536ab3d93fddd4
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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