Sodium Acetate → HCID 14578878, compound

HRID 231779Notes

Reaction equation

HRID 231779 reaction equation
O=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][CH2:5][CH2:4][CH:3]1[CH2:13][C:14]([OH:16])=O.Cl.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][NH2:27])=[CH:22][CH:21]=1.C([O-])(=O)C.[Na+]>C(O)C>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[C:14](=[O:16])[CH2:13][CH:3]3[CH2:4][CH2:5][S:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[C:2]3=[N:27]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 14578871(5-Oxo-2,3,4,5-tetrahydro-1-benzothiepin-4-yl)acetic acid

Product 1

HCID 14578878HCID 14578878, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4 g of 5-oxo-2,3,4,5-tetrahydro-[1]benzothiepine-4-acetic acid, 3.5 g of 4-methoxyphenylhydrazine hydrochloride and 1.8 g of sodium acetate in 100 ml of ethanol is refluxed under heating for 12 hours and then the solvent is distilled off. To the residue is added 20 ml of acetic acid and the mixture is refluxed under heating for 2 hours. The solvent is distilled off, and the mixture of the residue in water is extracted with ethyl acetate. The organic layer is washed with water, dried over anhydrous magnesium sulfate and the solvent is distilled off. The crude product obtained is purified by column chromatography and recrystallized from ethanol to give 1.9 g of 2-(4-methoxyphenyl)-4,4a,5,6-tetrahydro-[1]benzothiepino[5,4-c]pyridazin-3(2H)-one, melting at 143°-145° C.

Workup

  1. temperatureis refluxed
  2. temperatureunder heating for 12 hours
  3. distillationthe solvent is distilled off
  4. additionTo the residue is added 20 ml of acetic acid
  5. temperaturethe mixture is refluxed
  6. temperatureunder heating for 2 hours
  7. distillationThe solvent is distilled off
  8. additionthe mixture of the residue in water
  9. extractionis extracted with ethyl acetate
  10. washThe organic layer is washed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationthe solvent is distilled off
  13. customThe crude product obtained
  14. customis purified by column chromatography
  15. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-87bcb676a4c24937aa4e846496e7af0f
Source dataset
uspto-grants-1989_07
Patent number
US04849421

Reaction notes

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