Hydrogen Sulfide → 10-[1-(2,5-Dihydro-1-pyrrolyl)-2-propyl]-2-phenothiazinecarbothioamide

HRID 704190Notes

Reaction equation

HRID 704190 reaction equation
[N:1]1([CH2:6][CH:7]([N:9]2[C:22]3[CH:21]=[C:20]([C:23]#[N: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][CH:4]=[CH:3][CH2:2]1.C(N(CC)CC)C.[SH2:32]>N1C=CC=CC=1>[N:1]1([CH2:6][CH:7]([N:9]2[C:22]3[CH:21]=[C:20]([C:23](=[S:32])[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][CH:4]=[CH:3][CH2:2]1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 53668602HCID 53668602, compound

Product 1

HCID 5405044010-[1-(2,5-Dihydro-1-pyrrolyl)-2-propyl]-2-phenothiazinecarbothioamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 10-[1-(2,5-dihydro-1-pyrrolyl)-2-propyl]-2-phenothiazinecarbonitrile, L series (12.57 g) and triethylamine (5.5 cc) in pyridine (115 cc) is treated with hydrogen sulphide by bubbling in for 2 hours. After 16 hours' stirring at a temperature in the region of 25° C., the light brown solution obtained is purged with nitrogen for 2 hours, diluted with ethyl acetate (300 cc), washed with distilled water (10×100 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The yellow product (13.3 g) of meringue-like consistency is purified by chromatography on a column (height: 47 cm; diameter: 3.8 cm) of silica gel (0.04-0.063 mm) under a slight excess pressure of nitrogen (40 kPa), eluting with ethyl acetate (2 liters) and collecting 125-cc fractions. Fractions 4 to 10 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give 10-[1-(2,5-dihydro-1-pyrrolyl)-2-propyl]-2-phenothiazinecarbothioamide, L series (10.6 g) in the form of a yellow product of meringue-like consistency.

Workup

  1. customby bubbling in for 2 hours
  2. customthe light brown solution obtained
  3. customis purged with nitrogen for 2 hours
  4. additiondiluted with ethyl acetate (300 cc)
  5. washwashed with distilled water (10×100 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  9. customThe yellow product (13.3 g) of meringue-like consistency is purified by chromatography on a column (height: 47 cm; diameter: 3.8 cm) of silica gel (0.04-0.063 mm) under a slight excess pressure of nitrogen (40 kPa)
  10. washeluting with ethyl acetate (2 liters)
  11. customcollecting 125-cc fractions
  12. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.

Sources & evidence

ORD record
ord-49836974b06e44caac7918da12bbd682
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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