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

HRID 866916Notes

Reaction equation

HRID 866916 reaction equation
[C:1]([C:3]1[C:8]2[CH2:9][C:10](=NN)[C:11]3[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:12]=3[S:13][C:7]=2[CH:6]=[CH:5][CH:4]=1)#N.[OH-:22].[Na+].C(O)C[O:26]CCO>O>[C:1]([C:3]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:12]=3[S:13][C:7]=2[CH:6]=[CH:5][CH:4]=1)([OH:26])=[O:22]

Participants

5

Reactant 3

HCID 8117Diethylene GlycolHCID 14798Sodium HydroxideHCID 867358609-Cyano-2-methoxy-10,11-dihydro-11-oxo-dibenzo[b,f]thiepin hydrazone

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

600mg of 9-cyano-2-methoxy-10,11-dihydro-11-oxo-dibenzo-[b,f]thiepin hydrazone and 600mg of sodium hydroxide were added to 10ml 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 extracted with benzene. The aqueous layer was acidified with hydrochloric acid and extracted with benzene. The benzene 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 chloroform-ether (10:1). There was obtained 9-carboxy-2-methoxy-10,11-dihydrodibenzo[b,f]thiepin. Recrystallization from benzene afforded 140mg of the desired product as colorless needles having a melting point of 185°-187° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureAfter cooling
  3. extractionwas extracted with benzene
  4. extractionextracted with benzene
  5. extractionThe benzene extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated
  9. customto obtain the residue, which
  10. customwas chromatographed over silica gel
  11. washeluted with chloroform-ether (10:1)

Sources & evidence

ORD record
ord-6a7ad72f30fc496b8ec46c31c93e84e0
Source dataset
uspto-grants-1978_07
Patent number
US04101667

Reaction notes

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