Water → 9-Carboxy-2-methoxy-10,11-dihydro-11-oxodibenzo[b,f]thiepin

HRID 903632Notes

Reaction equation

HRID 903632 reaction equation
[OH2:1].[OH-:2].[K+].[C:4]([C:6]1[C:11]2[CH2:12][C:13](=[O:23])[C:14]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:15]=3[S:16][C:10]=2[CH:9]=[CH:8][CH:7]=1)#N>C(O)C>[C:4]([C:6]1[C:11]2[CH2:12][C:13](=[O:23])[C:14]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:15]=3[S:16][C:10]=2[CH:9]=[CH:8][CH:7]=1)([OH:2])=[O:1]

Participants

5

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 126871079-Cyano-2-methoxy-10,11-dihydro-11-oxo-dibenzo[b,f]thiepin

Product 1

HCID 233370379-Carboxy-2-methoxy-10,11-dihydro-11-oxodibenzo[b,f]thiepin

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the mixture of 1 ml of water and 600 mg of potassium hydroxide in 9 ml of ethanol was added 200 mg of 9-cyano-2-methoxy-10,11-dihydro-11-oxo-dibenzo[b,f]thiepin and the resulting mixture was heated under reflux overnight. Water was added to the mixture, which was washed with benzene. Aqueous layer was acidified with hydrochloric acid, extracted with chloroform, washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated therefrom and there was obtained 130 mg of 9-carboxy-2-methoxy-10,11-dihydro-11-oxodibenzo[b,f]thiepin having a melting point of 157°-160° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux overnight
  3. washwas washed with benzene
  4. extractionextracted with chloroform
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-f597262873cd4584a743b6cb7e9202ac
Source dataset
uspto-grants-1980_10
Patent number
US04228284

Reaction notes

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