Hydrogen Sulfide → 10H-phenothiazine-2-carbothioamide

HRID 704165Notes

Reaction equation

HRID 704165 reaction equation
C(N(CC)CC([N:7]1[C:20]2[CH:19]=[C:18]([C:21]#[N:22])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)C)C.C(N(CC)CC)C.[SH2:32]>N1C=CC=CC=1>[CH:19]1[C:20]2[NH:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[S:14][C:15]=2[CH:16]=[CH:17][C:18]=1[C:21](=[S:32])[NH2:22]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 1453650710-(1-Diethylamino-2-propyl)-2-phenothiazinecarbonitrile

Product 1

HCID 2271158710H-phenothiazine-2-carbothioamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 10-[(2RS)-1-diethylamino-2-propyl]2-phenothiazinecarbonitrile (5.66 g) and triethylamine (2.35 cc) in pyridine (113 cc) is treated with hydrogen sulphide for 1 hour and then stirred for 3 days at a temperature in the region of 20° C. The greenish solution obtained is purged with nitrogen, poured into distilled water (500 cc) and extracted with ethyl acetate (2×500 cc). The combined organic phases are washed successively with distilled water (2×200 cc) and with saturated aqueous sodium chloride solution (200 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 (9.1 g) is purified by chromatography on a column (height: 25 cm, diameter: 3 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa), eluting with ethyl acetate (750 cc) and collecting 50-cc fractions. The combined fractions 4 to 10 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-[2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarbothioamide (6.2 g) is thereby obtained in the form of an orange oil.

Workup

  1. customThe greenish solution obtained
  2. customis purged with nitrogen
  3. additionpoured
  4. distillationinto distilled water (500 cc)
  5. extractionextracted with ethyl acetate (2×500 cc)
  6. washThe combined organic phases are washed successively with distilled water (2×200 cc) and with saturated aqueous sodium chloride solution (200 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 (9.1 g) is purified by chromatography on a column (height: 25 cm, diameter: 3 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa)
  11. washeluting with ethyl acetate (750 cc)
  12. customcollecting 50-cc fractions
  13. concentrationThe combined fractions 4 to 10 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-8004bd9b1dfd4fc7b039b2ebc2ec9d14
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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