Hydrogen Sulfide → HCID 14536602, compound

HRID 704199Notes

Reaction equation

HRID 704199 reaction equation
[N:1]1([CH2:6][CH:7]([N:9]2[C:22]3[CH:21]=[C:20]([C:23](=[S:25])[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][CH2:4][CH2:3][CH2:2]1.[CH3:26][CH:27]([CH3:31])[CH2:28][CH2:29]N.S>C(O)C>[CH3:26][CH:27]([CH3:31])[CH2:28][CH2:29][NH:24][C:23]([C:20]1[CH:19]=[CH:18][C:17]2[S:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH:7]([CH3:8])[CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:22]=2[CH:21]=1)=[S:25]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 7894IsoamylamineHCID 1453652810-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide

Product 1

HCID 14536602HCID 14536602, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide, L series (6 g) and 3-methylbutylamine (18.9 cc) in absolute ethanol (90 cc) is saturated with hydrogen sulphide and brought for 16 hour to a temperature in the region of 105° C. After cooling, the reaction mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The oily brown residue is purified by chromatography on a column (height: 40 cm; diameter: 4 cm) of silica gel (0.02-0.063 mm), eluting with methylene chloride (1 liter) and then with a mixture (95:5 by volume) (1.5 liters) of methylene chloride and methanol and collecting 80-cc fractions. Fractions 23 to 36 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. N-(3-Methylbutyl)-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide, L series (6.76 g) is thereby obtained in the form of an orange oil. 1 g of this oil is dissolved in ethyl acetate (10 cc), and a 3.3N solution (0.7 cc) of hydrochloric acid in isopropyl ether is introduced with stirring. After 30 minutes' stirring at a temperature in the region of 5° C., the crystals formed are drained, washed with diethyl ether (3×10 cc) and dried under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C. N-(3-Methylbutyl)-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide hydrochloride, L series (0.75 g) is thereby obtained in the form of yellow crystals, m.p. 186° C., the NMR spectrum of which is identical to that of the product obtained in Example 35.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  3. customThe oily brown residue is purified by chromatography on a column (height: 40 cm; diameter: 4 cm) of silica gel (0.02-0.063 mm)
  4. washeluting with methylene chloride (1 liter)
  5. customwith a mixture (95:5 by volume) (1.5 liters) of methylene chloride and methanol and collecting 80-cc fractions
  6. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-133e0318168d42db9c219cdd764ff313
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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