Water → HCID 12687092, compound

HRID 866925Notes

Reaction equation

HRID 866925 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

1.0g of 9-cyano-3 -fluoro-10,11-dihydrodibenzo[b,f]thiepin-11-one hydrazone and 1.0g of sodium hydroxide were added to 15ml 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 180mg 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-8a8a86d0fcfa475aba3345a1f30b018c
Source dataset
uspto-grants-1978_07
Patent number
US04101667

Reaction notes

Loading…