Hydrogen Sulfide → 10-((2RS)-1-[N-Ethyl-N-(1-methylethyl)-amino]-2-propyl}-2-phenothiazinecarbothioamide

HRID 704175Notes

Reaction equation

HRID 704175 reaction equation
[CH2:1]([N:3]([CH2:7][CH:8]([N:10]1[C:23]2[CH:22]=[C:21]([C:24]#[N:25])[CH:20]=[CH:19][C:18]=2[S:17][C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH3:9])[CH:4]([CH3:6])[CH3:5])[CH3:2].C(N(CC)CC)C.[SH2:33]>N1C=CC=CC=1>[CH2:1]([N:3]([CH2:7][CH:8]([N:10]1[C:23]2[CH:22]=[C:21]([C:24](=[S:33])[NH2:25])[CH:20]=[CH:19][C:18]=2[S:17][C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH3:9])[CH:4]([CH3:5])[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 15925265HCID 15925265, compound

Product 1

HCID 1592526210-((2RS)-1-[N-Ethyl-N-(1-methylethyl)-amino]-2-propyl}-2-phenothiazinecarbothioamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 10-{(2RS)-1-[N-ethyl-N-(1-methylethyl)amino]-2-propyl}-2-phenothiazinecarbonitrile (2.3 g) and triethylamine in anhydrous pyridine (46 cc) is treated with hydrogen sulphide and stirred for 16 hours at a temperature in the region of 20° C. The greenish solution obtained is purged with nitrogen, poured into distilled water (200 cc) and extracted with ethyl acetate (200 cc and then 100 cc). The combined organic phases are washed with distilled water (3×100 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual yellow oil (4 g) is purified by chromatography on a column (height: 25 cm; diameter: 4 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa), eluting with a mixture (75:25 by volume) (750 cc) of ethyl acetate and cyclohexane and collecting 60-cc fractions. The combined fractions 6 to 10 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-((2RS)-1-[N-Ethyl-N-(1-methylethyl)-amino]-2-propyl}-2-phenothiazinecarbothioamide (2.5 g) is thereby obtained in the form of a yellow oil.

Workup

  1. customThe greenish solution obtained
  2. customis purged with nitrogen
  3. additionpoured
  4. distillationinto distilled water (200 cc)
  5. extractionextracted with ethyl acetate (200 cc
  6. washThe combined organic phases are washed with distilled water (3×100 cc)
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  10. customThe residual yellow oil (4 g) is purified by chromatography on a column (height: 25 cm; diameter: 4 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa)
  11. washeluting with a mixture (75:25 by volume) (750 cc) of ethyl acetate and cyclohexane
  12. customcollecting 60-cc fractions
  13. concentrationThe combined fractions 6 to 10 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-04276a122eef463580bfba8857755647
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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