Hydrogen Sulfide → HCID 14536624, compound

HRID 728734Notes

Reaction equation

HRID 728734 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.[ClH:26].[CH3:27][CH:28]([CH3:33])[CH2:29][CH2:30][CH2:31]N.S>C(O)C>[ClH:26].[CH3:27][CH:28]([CH3:33])[CH2:29][CH2:30][CH2:31][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]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 126557894-methylpentan-1-amine hydrochlorideHCID 1453652810-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide

Product 1

HCID 14536624HCID 14536624, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10-[(2RS)-l-(l-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (2 g) and 4-methylpentylamine hydrochloride (7.4 g) in absolute ethanol (30 cc) is saturated with hydrogen sulphide. The reaction mixture is then brought for 16 hours to a temperature in the region of 105° C. After being cooled, it is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The pasty residue (5 g) is purified by chromatography on a column (height: 35 cm; diameter 3 cm) of silica gel (0.2-0.063 mm), eluting successively with methylene chloride (500 cc) and then with a mixture (95:5 by volume) (500 cc) of methylene chloride and methanol and collecting 30-cc fractions. Fractions 25 to 28 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual orange oil (2.16 g) is dissolved in ethyl acetate (10 cc) and there is added, with stirring, a 3.3N solution (1.5 cc) of hydrochloric acid in isopropyl ether followed by ethyl ether until a persistent cloudiness is formed. After 1 hour at a temperature in the region of 5° C., the solid formed is drained, washed with ethyl ether (3×10 cc) and dried under reduced pressure (5mm Hg; 0.7 kPa) at 40° C. N-(4-Methylpentyl)-l0-[(2RS)-l-(l-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide hydrochloride (1.7 g) is thereby obtained in the form of a yellow solid, m.p. 186° C.

Workup

  1. temperatureAfter being cooled
  2. concentrationit is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  3. customThe pasty residue (5 g) is purified by chromatography on a column (height: 35 cm; diameter 3 cm) of silica gel (0.2-0.063 mm)
  4. washeluting successively with methylene chloride (500 cc)
  5. customwith a mixture (95:5 by volume) (500 cc) of methylene chloride and methanol and collecting 30-cc fractions
  6. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  7. dissolutionThe residual orange oil (2.16 g) is dissolved in ethyl acetate (10 cc)
  8. additionthere is added
  9. customis formed
  10. waitAfter 1 hour at a temperature in the region of 5° C.
  11. customthe solid formed
  12. washwashed with ethyl ether (3×10 cc)
  13. customdried under reduced pressure (5mm Hg; 0.7 kPa) at 40° C

Sources & evidence

ORD record
ord-5833786e13d540fc9bb5e8ac2fd95f59
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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