Water → HCID 12687102, compound

HRID 261554Notes

Reaction equation

HRID 261554 reaction equation
[C:1]([C:3]1[C:8]2[CH2:9][C:10](=NN)[C:11]3[CH:17]=[CH:16]C=C(F)[C:12]=3[S:13][C:7]=2[CH:6]=[CH:5][CH:4]=1)#N.[OH-:21].[Na+].[OH2:23].C(O)CO[CH2:27][CH2:28][OH:29]>>[C:1]([C:3]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:17]=[CH:16][CH:27]=[C:28]([OH:29])[C:12]=3[S:13][C:7]=2[CH:6]=[CH:5][CH:4]=1)([OH:23])=[O:21]

Participants

5

Reactant 4

HCID 962WaterHCID 8117Diethylene Glycol2×HCID 14798Sodium HydroxideHCID 54227800HCID 54227800, compound

Product 1

HCID 12687102HCID 12687102, compound

Procedure

500 mg of 9-cyano-4-fluoro-10,11-dihydrodibenzo[b,f]thiepin-11-one hydrazone was dissolved in 5 ml of diethylene glycol and to this mixture was added 500 mg of sodium hydroxide in 5 ml of diethylene glycol. The reaction mixture was heated with stirring at 180°-200° C. for 2 hours. After cooling, 30 ml of water was added to the mixture, which was extracted with benzene. The aqueous layer was acidified with conc. hydrochloric acid, extracted with ethyl acetate and the extract was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain glutinous residue, which was chromatographed over silica gel and eluted with benzene-ethyl acetate (1:1). Recrystallization from diluted methanol solution of the crude product obtained from a first fraction afforded 80 mg of 9-carboxy-4-hydroxy-10,11-dihydrodibenzo[b,f]thiepin having a melting point of 171°-173° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureAfter cooling
  3. extractionwas extracted with benzene
  4. extractionextracted with ethyl acetate
  5. washthe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customto obtain glutinous residue, which
  9. customwas chromatographed over silica gel
  10. washeluted with benzene-ethyl acetate (1:1)
  11. customRecrystallization from diluted methanol solution of the crude product
  12. customobtained from a first fraction

Sources & evidence

ORD record
ord-cf379903e7b44cb1bb8a40d16c28df9c
Source dataset
uspto-grants-1979_08
Patent number
US04166127

Reaction notes

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