Hydrogen Sulfide → HCID 14536608, compound

HRID 1109537Notes

Reaction equation

HRID 1109537 reaction equation
[N:1]1([CH2:6][CH:7]([N:9]2[C:22]3[CH:21]=[C:20]([C:23]([NH2:25])=[O: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:25][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)=[O:24]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 7894IsoamylamineHCID 20074882HCID 20074882, compound

Product 1

HCID 14536608HCID 14536608, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide, L series (6 g), and 3-methylbutylamine (18.9 cc) in absolute ethanol (90 cc) is saturated with hydrogen sulphide and brought for 16 hours 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 (1.5 liters) of methylene chloride and methanol (95:5 by volume) 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-phenothiazinecarboxamide, L series (6.76 g), is thereby obtained in the form of an orange-colored oil.

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 (1.5 liters) of methylene chloride and methanol (95:5 by volume) 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-ecd15bfc75b147f084bde75f8c49322b
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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