Hydrogen Sulfide → HCID 14536531, compound

HRID 704184Notes

Reaction equation

HRID 704184 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.[CH2:26](N)[CH2:27][CH3:28].S>C(O)C>[CH2:26]([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])[CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 7852PropylamineHCID 1453652810-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide

Product 1

HCID 14536531HCID 14536531, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide, D series (2.5 g) and propylamine (8.3 cc) in absolute ethanol (50 cc) is saturated with hydrogen sulphide and heated for 16 hours to a temperature in the region of 100° C. After cooling, the orange solution obtained is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual brown oil is purified by chromatography on a column (height: 25 cm; diameter: 2 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa), eluting with a mixture (80:20 by volume) (1 liter) of ethyl acetate and cyclohexane and collecting 40-cc fractions. The combined fractions 8 to 18 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. N-Propyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide, D series (2.4 g) is thereby obtained in the form of a yellow oil {[α]D20 =22±0.5° (0.06%; methanol)}. This oil is dissolved in 2-propanol (7.5 cc) at a temperature in the region of 50° C., and this solution is poured with stirring into a solution of fumaric acid (0.68 g) in 2-propanol (7.5 cc) at a temperature in the region of 60° C. Stirring is continued for 2 hours at a temperature in the region of 5° C. The solid formed is drained, washed with 2-propanol (2×2 cc) and dried under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C. N-Propyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide acid fumarate, D series (2 g) is thereby obtained in the form of a yellow solid, m.p. 206° C., the NMR characteristics of which are identical to those described in Example 13.

Workup

  1. temperatureAfter cooling
  2. customthe orange solution obtained
  3. concentrationis concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  4. customThe residual brown oil is purified by chromatography on a column (height: 25 cm; diameter: 2 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa)
  5. washeluting with a mixture (80:20 by volume) (1 liter) of ethyl acetate and cyclohexane
  6. customcollecting 40-cc fractions
  7. concentrationThe combined fractions 8 to 18 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-3ebac77bd1fd4653b97185a25cf10d20
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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