Hydrogen Sulfide → HCID 15925266, compound

HRID 704178Notes

Reaction equation

HRID 704178 reaction equation
[CH3:1][N:2]([CH2:6][CH:7]([N:9]1[C:22]2[CH:21]=[C:20]([C:23]#[N:24])[CH:19]=[CH:18][C:17]=2[S:16][C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH3:8])[CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[SH2:32]>N1C=CC=CC=1>[CH3:1][N:2]([CH2:6][CH:7]([N:9]1[C:22]2[CH:21]=[C:20]([C:23](=[S:32])[NH2:24])[CH:19]=[CH:18][C:17]=2[S:16][C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH3:8])[CH2:3][CH2:4][OH:5]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 15925269HCID 15925269, compound

Product 1

HCID 15925266HCID 15925266, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 10-{(2RS)-1-[N-methyl-N-(2-hydroxyethyl)amino]-2-propyl}-2-phenothiazinecarbonitrile (3.1 g) and triethylamine (1.3 cc) in anhydrous pyridine (62 cc) is treated with hydrogen sulphide. The greenish solution obtained is then stirred for 16 hours at a temperature in the region of 20° C., purged with nitrogen, poured into distilled water (500 cc) and extracted with ethyl acetate (2×250 cc). The combined organic phases are washed successively with distilled water (2×100 cc) and with saturated aqueous sodium chloride solution (100 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual orange oil (4.8 g) is purified by chromatography on a column (height: 30 cm, diameter: 2.8 cm) of silica gel (0.2-0.063 mm), eluting with a mixture (75:25 by volume) (3 liters) of ethyl acetate and cyclohexane and collecting 50-cc fractions. The combined fractions 19 to 50 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-{(2RS)-1-[N-methyl-N-(2-hydroxyethyl)amino]-2-propyl}-2-phenothiazinecarbothioamide (2.2 g) is thereby obtained in the form of a yellow product of meringue-like consistency.

Workup

  1. customThe greenish solution obtained
  2. custompurged with nitrogen
  3. additionpoured
  4. distillationinto distilled water (500 cc)
  5. extractionextracted with ethyl acetate (2×250 cc)
  6. washThe combined organic phases are washed successively with distilled water (2×100 cc) and with saturated aqueous sodium chloride solution (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 orange oil (4.8 g) is purified by chromatography on a column (height: 30 cm, diameter: 2.8 cm) of silica gel (0.2-0.063 mm)
  11. washeluting with a mixture (75:25 by volume) (3 liters) of ethyl acetate and cyclohexane
  12. customcollecting 50-cc fractions
  13. concentrationThe combined fractions 19 to 50 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-776af95487b840c0a5799a1b06fffff6
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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