Hydrogen Sulfide → HCID 14536559, compound

HRID 728714Notes

Reaction equation

HRID 728714 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][CH3:29].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][CH3:29]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8007ButylamineHCID 1453652810-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide

Product 1

HCID 14536559HCID 14536559, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (1 g) and butylamine (1.5 cc) in absolute ethanol (20 cc) is saturated with hydrogen sulphide and then heated for 24 hours to a temperature in the region of 120° C. After being cooled, the reaction mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is taken up with distilled water (10 cc) and ethyl acetate (25 cc). After extraction, the organic phase is separated, washed with distilled water (10 cc) and then with saturated aqueous sodium chloride solution (20 cc), dried over potassium carbonate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. N-Butyl-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (1.15 g) is thereby obtained in the form of a viscous yellow oil which is subsequently used as it is.

Workup

  1. temperatureAfter being cooled
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  3. extractionAfter extraction
  4. customthe organic phase is separated
  5. washwashed with distilled water (10 cc)
  6. dry with materialwith saturated aqueous sodium chloride solution (20 cc), dried over potassium carbonate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-2dd0a0b811b54968a78b52f9f75a72f9
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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