Acetic Acid → HCID 14536564, compound

HRID 728713Notes

Reaction equation

HRID 728713 reaction equation
[CH2:1]([NH:5][C:6]([C:8]1[CH:21]=[CH:20][C:19]2[S:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH:22]([CH3:29])[CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:10]=2[CH:9]=1)=S)[CH2:2][CH2:3][CH3:4].C(O)(=[O:32])C>C(OCC)C>[CH2:1]([NH:5][C:6]([C:8]1[CH:21]=[CH:20][C:19]2[S:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH:22]([CH3:29])[CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:10]=2[CH:9]=1)=[O:32])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 14536559HCID 14536559, compound

Product 1

HCID 14536564HCID 14536564, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of N-butyl-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (1.2 g) and mercuric acetate (1 g) in acetic acid (15 cc) is stirred for 5 hours at a temperature in the region of 20° C. The black suspension obtained is diluted with ethyl ether (25 cc) and filtered. The solid is washed with ethyl ether (2×10 cc). The combined organic phases are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C. The residue is taken up with ethyl acetate (25 cc) and distilled water (25 cc). The organic phase is separated, filtered, dried over magnesium sulphate, filtered again and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The very viscous residual oil (1.1 g) is taken up with a mixture (83:17 by volume) (12 cc) of ethyl acetate and methanol warmed to about 50° C. After 1 hour at a temperature in the region of 20° C., the solid formed is drained, washed with diethyl ether (2×10 cc) and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C. N-butyl-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]- 2-phenothiazinecarboxamide (0.4 g) is thereby obtained in the form o cream-coloured crystals, m.p. 218° C.

Workup

  1. customThe black suspension obtained
  2. filtrationfiltered
  3. washThe solid is washed with ethyl ether (2×10 cc)
  4. concentrationThe combined organic phases are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C
  5. distillationdistilled water (25 cc)
  6. customThe organic phase is separated
  7. filtrationfiltered
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered again
  10. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  11. temperaturewarmed to about 50° C
  12. waitAfter 1 hour at a temperature in the region of 20° C.
  13. customthe solid formed
  14. washwashed with diethyl ether (2×10 cc)
  15. customdried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C

Sources & evidence

ORD record
ord-fe89b5171f104ad182e3b94b82aa383e
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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