Hydrogen Sulfide → HCID 54318968, compound

HRID 704229Notes

Reaction equation

HRID 704229 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH2:8].S.[OH:10][CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH2:17][CH:18]([N:20]1[C:33]2[CH:32]=[C:31]([C:34](=S)N)[CH:30]=[CH:29][C:28]=2[S:27][C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH3:19]>C(OCC)(=O)C>[NH:1]1[CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]2[N:8]=[C:34]1[C:31]1[CH:30]=[CH:29][C:28]2[S:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH:18]([CH3:19])[CH2:17][N:13]3[CH2:14][CH2:15][CH2:16][C@@H:12]3[CH2:11][OH:10])[C:33]=2[CH:32]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 46101,2-DiaminocyclohexaneHCID 54075963HCID 54075963, compound

Product 1

HCID 54318968HCID 54318968, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

1,2-Diaminocyclohexane (10.57 g) is added to an ethanolic solution (40 cc), saturated with hydrogen sulphide, of 10-{1-[(2R)-2-hydroxymethyl-1-pyrrolidinyl]-2-propyl}-2-phenothiazinecarbothioamide, D series (3.65 g). The mixture is heated in an autoclave to 150° C. for 11 hours, then diluted with ethyl acetate (250 cc) and washed with distilled water (4×200 cc). The organic phase is separated after settling has taken place, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is diluted in boiling absolute ethanol (200 cc) and a small amount of insoluble matter is filtered off. The filtrate is stirred at 25° C. for 2 hours and then cooled to 5° C. for 12 hours. The precipitate formed is filtered off, washed with cold ethanol (3×10 cc) and dried under reduced pressure (5 mm Hg; 0.67 kPa) at 40° C. to give 2-(3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-2-yl)-10-{1-[(2R)-2-(hydroxymethyl)pyrrolidinyl]-2-propyl}phenothiazine, D series (1.1 g) in the form of a cream-coloured solid.

Workup

  1. washwashed with distilled water (4×200 cc)
  2. customThe organic phase is separated after settling
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  6. additionThe residue is diluted
  7. filtrationa small amount of insoluble matter is filtered off
  8. temperaturecooled to 5° C. for 12 hours
  9. customThe precipitate formed
  10. filtrationis filtered off
  11. washwashed with cold ethanol (3×10 cc)
  12. customdried under reduced pressure (5 mm Hg; 0.67 kPa) at 40° C.

Sources & evidence

ORD record
ord-779c5559524f44a8b609177038ee5348
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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