Water → HCID 14502136, compound

HRID 1165789Notes

Reaction equation

HRID 1165789 reaction equation
C([O-])(=O)C1C(=CC=CC=1)C([O-])=[O:5].[C:13]([C:15]1[CH:28]=[CH:27][C:26]2SC3C(=CC=CC=3)N(C[C@]([NH3+])(CCC)C3C=CC=CC=3)[C:17]=2[CH:16]=1)#[N:14].C([C:43]1[CH:56]=[CH:55][C:54]2[S:53][C:52]3[C:47](=[CH:48]C=CC=3)[N:46](C[C@@]([NH3+])(C3C=CC=CC=3)CCC)[C:45]=2[CH:44]=1)#N.[OH-].[K+].O>C(O)C>[OH:5][CH2:48][CH:47]([N:46]1[C:27]2[CH:28]=[C:15]([C:13]#[N:14])[CH:16]=[CH:17][C:26]=2[S:53][C:54]2[C:45]1=[CH:44][CH:43]=[CH:56][CH:55]=2)[CH3:52]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 86743821HCID 86743821, compound

Product 1

HCID 14502136HCID 14502136, compoundYield 127%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(-)-2-(2-cyano-10-phenothiazinyl)-1-propyl 1-phenyl-(S)-ethylammonium phthalate (95.4 g) is added to a solution of 23.5 g of potassium hydroxide in 1150 cc ethanol under reflux and reflux is continued while stirring for 10 minutes. The reaction mixture is then poured into iced water (1 liter) and extracted with ethyl acetate (2 liters and then 500 cc). The combined organic phases are washed successively with a 0.1N aqueous solution of hydrochloric acid (2×500 cc), with a saturated aqueous solution of sodium bicarbonate (2×500 cc) and with a saturated aqueous solution of sodium chloride (500 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual yellow solid (44 g) is taken up in isopropyl ether (200 cc) under reflux and the product crystallizes whilst warm. The mixture is allowed to return to a temperature of about 20° C. and the solid is centrifuged, washed with isopropyl ether (20 cc) and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 20° C. D series 10-(1-hydroxy-2-propyl)-2-phenothiazinecarbonitrile (36.5 g) is thus obtained in the form of yellow crystals which melt at 135° C.

Workup

  1. temperatureunder reflux
  2. temperaturereflux
  3. extractionextracted with ethyl acetate (2 liters
  4. washThe combined organic phases are washed successively with a 0.1N aqueous solution of hydrochloric acid (2×500 cc), with a saturated aqueous solution of sodium bicarbonate (2×500 cc) and with a saturated aqueous solution of sodium chloride (500 cc)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  8. temperatureunder reflux
  9. customthe product crystallizes
  10. temperaturewhilst warm
  11. customto return to a temperature of about 20° C.
  12. washwashed with isopropyl ether (20 cc)
  13. customdried under reduced pressure (5 mm Hg; 0.7 kPa) at 20° C

Sources & evidence

ORD record
ord-d65fb48895c9425f91f7f2f3b5fa5be8
Source dataset
uspto-grants-1990_03
Patent number
US04912105

Reaction notes

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