Water → HCID 12687092, compound

HRID 261558Notes

Reaction equation

HRID 261558 reaction equation
[C:1]([C:3]1[C:8]2[CH2:9][C:10](=NN)[C:11]3[CH:17]=CC(F)=[CH:14][C:12]=3[S:13][C:7]=2[CH:6]=[CH:5][CH:4]=1)#N.[OH-:21].[Na+].C(O)CO[CH2:26][CH2:27][OH:28].[OH2:30]>>[C:1]([C:3]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:17]=[CH:26][C:27]([OH:28])=[CH:14][C:12]=3[S:13][C:7]=2[CH:6]=[CH:5][CH:4]=1)([OH:30])=[O:21]

Participants

5

Reactant 4

HCID 962WaterHCID 8117Diethylene GlycolHCID 14798Sodium HydroxideHCID 53670505HCID 53670505, compound

Product 1

HCID 12687092HCID 12687092, compound

Procedure

1.0 g of 9-cyano-3-fluoro-10,11-dihydrodibenzo[b,f]thiepin-11-one hydrazone and 1.0 g of sodium hydroxide were added to 15 ml of diethylene glycol and the resulting mixture was heated with stirring at 190°-200° C. for 5 hours. After cooling, water was added to the mixture, which was washed with benzene. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain the residue, which was chromatographed over silica gel and eluted with benzene-ethyl acetate (3:2), and there was obtained crude product. Recrystallization from ethanol-water afforded 180 mg of 9-carboxy-3-hydroxy-10,11-dihydrodibenzo[b,f]thiepin having a melting point of 219°-221° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureAfter cooling
  3. washwas washed 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 the residue, which
  9. customwas chromatographed over silica gel
  10. washeluted with benzene-ethyl acetate (3:2)
  11. customthere was obtained crude product
  12. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-25f715e57101484d9685e8f08746460a
Source dataset
uspto-grants-1979_08
Patent number
US04166127

Reaction notes

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