Hydrazine hydrate (1:1) → HCID 12443712, compound

HRID 355103Notes

Reaction equation

HRID 355103 reaction equation
O=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[S:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18]([OH:20])=[O:19])=[CH:16][C:3]1=2.O.NN>C(O)C>[CH:16]1[C:3]2[CH2:2][CH2:8][C:7]3[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=3[S:5][C:4]=2[CH:13]=[CH:14][C:15]=1[CH2:17][C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13134773HCID 13134773, compound

Product 1

HCID 12443712HCID 12443712, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 400 mg of (10,11-dihydro-11-oxo dibenzo[b,f]thiepin-2-yl)-acetic acid were added 20 ml of ethanol and 1 ml of hydrazine hydrate, and the mixture was refluxed with stirring under a dry atmosphere for 5 hours. After cooling, the solvent was removed by distillation under reduced pressure, and to the resulting mixture were added 20 ml of diethylene glycol and 4.0 g of sodium hydroxide. Thereafter, the resulting mixture was stirred under a dry atmosphere at 130° C. for 2 hours. After subsequent cooling, water was added to the mixture which was then washed with ethyl acetate. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a residue, which was chromatographed over 18 g of silica gel and eluted with n-hexane/acetone (5/1) to obtain pale yellow crystals. These crystals were recrystallized from acetone/n-hexane to give 321 mg (yield: 84%) of (10,11-dihydro dibenzo[b,f]-thiepin-2-yl)-acetic acid as colorless crystals having a melting point of 111°-112° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureAfter cooling
  3. customthe solvent was removed by distillation under reduced pressure
  4. additionto the resulting mixture were added 20 ml of diethylene glycol and 4.0 g of sodium hydroxide
  5. stirringThereafter, the resulting mixture was stirred under a dry atmosphere at 130° C. for 2 hours
  6. additionAfter subsequent cooling, water was added to the mixture which
  7. washwas then washed with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with a saturated sodium chloride solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThe solvent was distilled off under reduced pressure
  12. customto obtain a residue, which
  13. customwas chromatographed over 18 g of silica gel
  14. washeluted with n-hexane/acetone (5/1)
  15. customto obtain pale yellow crystals
  16. customThese crystals were recrystallized from acetone/n-hexane

Sources & evidence

ORD record
ord-42c3102fe3a84ad0a7a6065101f3765b
Source dataset
uspto-grants-1983_03
Patent number
US04377702

Reaction notes

Loading…