Hydrazine hydrate (1:1) → HCID 12687089, compound

HRID 866919Notes

Reaction equation

HRID 866919 reaction equation
[C:1]([C:4]1[C:9]2[CH2:10][C:11](=O)[C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[S:14][C:8]=2[CH:7]=[CH:6][CH:5]=1)([OH:3])=[O:2].O.NN>C(O)C>[C:1]([C:4]1[C:9]2[CH2:10][CH2:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[S:14][C:8]=2[CH:7]=[CH:6][CH:5]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 23337049HCID 23337049, compound

Product 1

HCID 12687089HCID 12687089, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 1.0g of 9-carboxy-10,11-dihydro-11-oxodibenzo[b,f]thiepin, 1.0g of hydrazine hydrate and 30ml of ethanol was heated under reflux on water bath for 4 hours. The reaction mixture was concentrated to about 15ml to separate crystals on cooling, which were collected by filtration. They were added to the mixture of 1.0g of sodium hydroxide and 20ml of diethylene glycal and the resulting mixture was heated with stirring at 190°-200° C for 2 hours. After cooling, 300ml of water was added to the mixture, which was extracted with diethyl ether. The aqueous layer was acidified with conc. hydrochloric acid and extracted with chloroform and the solvent was evaporated therefrom. The thus obtained residue was chromatographed over silica gel and eluted with benzene-ethyl acetate (1:1), and there was obtained 0.4g of 9-carboxy-10,11-dihydrodibenzo[b,f]thiepin as yellow prismatic crystals having a melting point of 186°-187° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux on water bath for 4 hours
  3. concentrationThe reaction mixture was concentrated to about 15ml
  4. customto separate crystals
  5. temperatureon cooling
  6. filtrationwhich were collected by filtration
  7. additionThey were added to the mixture of 1.0g of sodium hydroxide and 20ml of diethylene glycal
  8. temperaturethe resulting mixture was heated
  9. temperatureAfter cooling
  10. addition300ml of water was added to the mixture, which
  11. extractionwas extracted with diethyl ether
  12. extractionextracted with chloroform
  13. customthe solvent was evaporated
  14. customThe thus obtained residue was chromatographed over silica gel
  15. washeluted with benzene-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-1a0ec6d3fe2a4c3cb9753d1c662e1020
Source dataset
uspto-grants-1978_07
Patent number
US04101667

Reaction notes

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