Hydrogen Sulfide → 10-[(1RS)-2-hydroxy-1-methylethyl]-2-phenothiazinecarbothioamide

HRID 1109550Notes

Reaction equation

HRID 1109550 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][CH:10]([N:12]1[C:25]2[CH:24]=[C:23]([C:26]#[N:27])[CH:22]=[CH:21][C:20]=2[S:19][C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:11].[SH2:28]>N1C=CC=CC=1>[OH:8][CH2:9][CH:10]([N:12]1[C:25]2[CH:24]=[C:23]([C:26](=[S:28])[NH2:27])[CH:22]=[CH:21][C:20]=2[S:19][C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:11]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 14502136HCID 14502136, compound

Product 1

HCID 1509623010-[(1RS)-2-hydroxy-1-methylethyl]-2-phenothiazinecarbothioamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Triethylamine (98.4 cc) is added to a solution of 10-[(1RS)-2-hydroxy-1-methylethyl]-2-phenothiazine-carbonitrile (197.7 g) in anhydrous pyridine (750 cc), and hydrogen sulphide is bubbled through for 6 hours 30 minutes at 25° C. while the mixture is kept stirred. The mixture is stirred for 16 hours at 25° C., then purged with a stream of nitrogen for 2 hours and poured into distilled water (3000 cc). The oil which forms is separated after settling has taken place, washed with distilled water (3×1000 cc) and dissolved in ethyl acetate (3000 cc). The solution obtained is washed with distilled water (7×1 liter), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give a yellow crystalline mass (225 g). This product is recrystallized in ethanol (1350 cc) to give 10-[(1RS)-2-hydroxy-1 -methylethyl]-2-phenothiazinecarbothioamide (158.4 g) in the form of yellow crystals, m.p. 152° C.

Workup

  1. customis bubbled through for 6 hours 30 minutes at 25° C. while the mixture
  2. stirringThe mixture is stirred for 16 hours at 25° C.
  3. custompurged with a stream of nitrogen for 2 hours
  4. additionpoured
  5. distillationinto distilled water (3000 cc)
  6. customThe oil which forms is separated after settling
  7. washwashed with distilled water (3×1000 cc)
  8. dissolutiondissolved in ethyl acetate (3000 cc)
  9. customThe solution obtained
  10. washis washed with distilled water (7×1 liter)
  11. dry with materialdried over magnesium sulphate
  12. filtrationfiltered
  13. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  14. customto give a yellow crystalline mass (225 g)
  15. customThis product is recrystallized in ethanol (1350 cc)

Sources & evidence

ORD record
ord-f64accb4a78e4ae89f4b62d6daabe862
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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