Hydrogen Sulfide → 10-(1-diethylamino-2-propyl)-N-(3-methyl-1-butyl)-2-phenothiazinecarbothioamide

HRID 1109540Notes

Reaction equation

HRID 1109540 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4]N.[CH2:7]([N:9]([CH2:30][CH3:31])[CH2:10][CH:11]([N:13]1[C:26]2[CH:25]=[C:24]([C:27](=[S:29])[NH2:28])[CH:23]=[CH:22][C:21]=2[S:20][C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH3:12])[CH3:8].S>C(O)C>[CH2:30]([N:9]([CH2:7][CH3:8])[CH2:10][CH:11]([N:13]1[C:26]2[CH:25]=[C:24]([C:27](=[S:29])[NH:28][CH2:4][CH2:3][CH:2]([CH3:6])[CH3:1])[CH:23]=[CH:22][C:21]=2[S:20][C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH3:12])[CH3:31]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 7894IsoamylamineHCID 1453651110-(1-Diethylamino-2-propyl)-2-phenothiazinecarbothioamide

Product 1

HCID 1453659310-(1-diethylamino-2-propyl)-N-(3-methyl-1-butyl)-2-phenothiazinecarbothioamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Methylbutylamine (10.7 cc) is added to a solution of 10-(1-diethylamino-2-propyl)-2-phenothiazinecarbothioamide acid fumarate, L series (3 g), in absolute ethanol (45 cc) and this solution is saturated with hydrogen sulphide. The mixture is then brought to a temperature in the region of 105° C. for 16 hours and concentrated to dryness under reduced pressure (30 mm Hg; 4 pKa). The residual orange-colored oil is purified by chromatography on a column (height: 35 cm; diameter: 3 cm) of silica gel (0.2-0.063 mm), eluting with mixture (400 cc) of ethyl acetate and cyclohexane (70:30 by volume) and collecting 30-cc fractions. Fractions 7 to 11 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 pKa) at 50° C. to give 10-(1-diethylamino-2-propyl)-N-(3-methyl-1-butyl)-2-phenothiazinecarbothioamide, L series (3.1 g), in the form of an orange-colored oil.

Workup

  1. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 pKa)
  2. customThe residual orange-colored oil is purified by chromatography on a column (height: 35 cm; diameter: 3 cm) of silica gel (0.2-0.063 mm)
  3. washeluting with mixture (400 cc) of ethyl acetate and cyclohexane (70:30 by volume)
  4. customcollecting 30-cc fractions
  5. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 pKa) at 50° C.

Sources & evidence

ORD record
ord-89865478b7314116b35f4bf15c8b1d2e
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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