Hydrogen Sulfide → N-(3-Methylbutyl)-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide

HRID 728727Notes

Reaction equation

HRID 728727 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[N:7]1([CH2:12][CH:13]([N:15]2[C:28]3[CH:27]=[C:26]([C:29](=[S:31])N)[CH:25]=[CH:24][C:23]=3[S:22][C:21]3[C:16]2=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH3:14])[CH2:11][CH2:10][CH2:9][CH2:8]1.S>C(O)C>[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:29]([C:26]1[CH:25]=[CH:24][C:23]2[S:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH:13]([CH3:14])[CH2:12][N:7]3[CH2:11][CH2:10][CH2:9][CH2:8]3)[C:28]=2[CH:27]=1)=[S:31]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 7894IsoamylamineHCID 1453652810-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide

Product 1

HCID 14536602N-(3-Methylbutyl)-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Methylbutylamine (12.9 cc) is added to a solution of 10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide, D series (4.1 g) in ethanol (61.5 cc), and the mixture is then saturated with hydrogen sulphide and heated for 16 hours to a temperature in the region of 105° C. After being cooled, the solution is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. A yellow oil is obtained, which is purified by chromatography on a column (height: 30 cc; diameter: 4 cm) of silica gel (0.2-0.063 mm), eluting with a mixture (95:5 by volume) (1.5 liters) of methylene chloride and methanol and collecting 80-cc fractions. Fractions 14 to 17 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. N-(3-Methylbutyl)-10-[1-(1-pyrrolidinyl)-2-propyl]-2phenothiazinecarbothioamide, D series (4.7 g) is obtained in the form of an orange oil.

Workup

  1. temperatureAfter being cooled
  2. concentrationthe solution is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  3. customA yellow oil is obtained
  4. customwhich is purified by chromatography on a column (height: 30 cc; diameter: 4 cm) of silica gel (0.2-0.063 mm)
  5. washeluting with a mixture (95:5 by volume) (1.5 liters) of methylene chloride and methanol
  6. customcollecting 80-cc fractions
  7. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-66fc4e364acd4beb91cb94ea0a73ced8
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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