Hydrogen Sulfide → 10-(1-Diethylamino-2-propyl)-2-phenothiazinecarbothioamide

HRID 728697Notes

Reaction equation

HRID 728697 reaction equation
[CH2:1]([N:3]([CH2:23][CH3:24])[CH2:4][CH:5]([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)[CH3:6])[CH3:2].C(N(CC)CC)C.[SH2:32]>N1C=CC=CC=1>[CH2:23]([N:3]([CH2:1][CH3:2])[CH2:4][CH:5]([N:7]1[C:20]2[CH:19]=[C:18]([C:21](=[S:32])[NH2:22])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:6])[CH3:24]

Participants

5

Reactant 3

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

Product 1

HCID 1453651110-(1-Diethylamino-2-propyl)-2-phenothiazinecarbothioamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 10-[(2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarbonitrile (8.44 g) and triethylamine (3.5 cc) in anhydrous pyridine (60 cc) is saturated by bubblin9 in hydrogen sulphide for 5 hours at 25° C. The clear solution obtained is kept stirred for 12 hours at 25° C., and the mixture is then outgassed by bubbling through nitrogen for 90 minutes. The reaction mixture i diluted with ethyl acetate (500 cc) and washed with distilled water (8×200 cc). The organic phase is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa). The residue is purified by chromatography on a column of basic alumina (0.05-0.16 mm) (height: 31 cm; diameter: 2.6 cm), eluting with mixtures of cyclohexane and ethyl acetate in proportions (by volume) of 80:20 (5 liters) and 50:50 (5 liters) and collecting 100-cc fractions. Fractions 4 to 90 are combined and concentrated under reduced pressure (30 mm Hg; 4 kPa) to give 10-[(2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarbothioamide (8.54 g) in the form of an orange-yellow product of honey-like consistency.

Workup

  1. customThe clear solution obtained
  2. customby bubbling through nitrogen for 90 minutes
  3. additionThe reaction mixture i diluted with ethyl acetate (500 cc)
  4. washwashed with distilled water (8×200 cc)
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa)
  8. customThe residue is purified by chromatography on a column of basic alumina (0.05-0.16 mm) (height: 31 cm; diameter: 2.6 cm)
  9. washeluting with mixtures of cyclohexane and ethyl acetate in proportions (by volume) of 80:20 (5 liters) and 50:50 (5 liters)
  10. customcollecting 100-cc fractions
  11. concentrationconcentrated under reduced pressure (30 mm Hg; 4 kPa)

Sources & evidence

ORD record
ord-e389d5df7d6c426f8ddba7f9bfa2452c
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

Loading…