Ethanol → Dibenzo(b,f)thiepin-1-carboxylic acid, 10,11-dihydro-8-methoxy-

HRID 261547Notes

Reaction equation

HRID 261547 reaction equation
C(O)C.[C:4]([C:7]1[C:12]2[CH2:13][C:14](=O)[C:15]3[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:16]=3[S:17][C:11]=2[CH:10]=[CH:9][CH:8]=1)([OH:6])=[O:5].O.NN>O1CCOCC1>[C:4]([C:7]1[C:12]2[CH2:13][CH2:14][C:15]3[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:16]=3[S:17][C:11]=2[CH:10]=[CH:9][CH:8]=1)([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 233370379-Carboxy-2-methoxy-10,11-dihydro-11-oxodibenzo[b,f]thiepin

Product 1

HCID 3045903Dibenzo(b,f)thiepin-1-carboxylic acid, 10,11-dihydro-8-methoxy-Yield 29.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the mixed solvent of 16 ml of ethanol and 16 ml of dioxane were added 1.8 g of 9-carboxy-2-methoxy-10,11-dihydro-11-oxo-dibenzo[b,f]thiepin and 2.0 g of hydrazine hydrate and the resulting mixture was heated under reflux for 8 hours. After the completion of reaction, the solvent was distilled off and 1.8 g of sodium hydroxide and 30 ml of diethylene glycol was added to the residue. The thus obtained mixture was heated under reflux at 190°-200° C. for 5 hours. After cooling, water was added to the mixture which was extracted benzene. The aqueous layer was acidified with hydrochloric acid and extracted with benzene. The extract was washed with water, dried and the solvent was distilled off. The thus obtained residue was chromatographed over silica gel, eluted with chloroform-diethylether (10:1), was obtained 0.5 g of 9carboxy-2-methoxy-10,11-dihydrodibenzo[b,f]thiepin as colorless needles having a melting point of 185°-187° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 8 hours
  3. customAfter the completion of reaction
  4. distillationthe solvent was distilled off
  5. addition1.8 g of sodium hydroxide and 30 ml of diethylene glycol was added to the residue
  6. temperatureThe thus obtained mixture was heated
  7. temperatureunder reflux at 190°-200° C. for 5 hours
  8. temperatureAfter cooling
  9. additionwater was added to the mixture which
  10. extractionwas extracted benzene
  11. extractionextracted with benzene
  12. washThe extract was washed with water
  13. customdried
  14. distillationthe solvent was distilled off
  15. customThe thus obtained residue was chromatographed over silica gel
  16. washeluted with chloroform-diethylether (10:1)

Sources & evidence

ORD record
ord-bd4c045825ae483ba04f5b0c10d9de25
Source dataset
uspto-grants-1979_08
Patent number
US04166127

Reaction notes

Loading…