Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → HCID 14098684, compound

HRID 1905374Notes

Reaction equation

HRID 1905374 reaction equation
O=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][CH2:4][CH:3]1[CH2:12][C:13]([OH:15])=O.Cl.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][NH2:25])=[CH:20][CH:19]=1.C([O-])(=O)C.[Na+]>C(O)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:13](=[O:15])[CH2:12][CH:3]3[CH2:4][S:5][C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[C:2]3=[N:25]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 517045Sodium AcetateHCID 14098683(4-Oxo-3,4-dihydro-2H-1-benzothiopyran-3-yl)acetic acid

Product 1

HCID 14098684HCID 14098684, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10 g of α-(2,3-dihydro-4-oxo-4H-1-benzothiopyran-3-yl)acetic acid, 12 g of 4-chlorophenyhydrazine hydrochloride and 5.5 g of sodium acetate in 200 ml of ethanol is refluxed under heating for 10 hours. The ethanol is distilled off under reduced pressure and to the residue is added 200 ml of acetic acid and the mixture is refluxed under heating for 10 hours. After the acetic acid is distilled off, the residue is extracted with chloroform. The extract is washed with water, dried over magnesium sulfate anhydride and the chloroform is distilled off under reduced pressure. To the precipitated crystals is added diisopropyl ether. The crystals are collected by filtration and recrystallized from acetic acid to give 11.5 g of 2-(4-chlorophenyl)-2,3,4,4a-tetrahydro-5H-(1)benzothiopyrano[4,3-c]pyridazin-3-one, melting at 146°-147° C., as colorless prisms.

Workup

  1. temperatureis refluxed
  2. temperatureunder heating for 10 hours
  3. distillationThe ethanol is distilled off under reduced pressure and to the residue
  4. additionis added 200 ml of acetic acid
  5. temperaturethe mixture is refluxed
  6. temperatureunder heating for 10 hours
  7. distillationAfter the acetic acid is distilled off
  8. extractionthe residue is extracted with chloroform
  9. washThe extract is washed with water
  10. dry with materialdried over magnesium sulfate anhydride
  11. distillationthe chloroform is distilled off under reduced pressure
  12. additionTo the precipitated crystals is added diisopropyl ether
  13. filtrationThe crystals are collected by filtration
  14. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-ebe553a56cc249f081dcdd2bbaae6de8
Source dataset
uspto-grants-1989_06
Patent number
US04843075

Reaction notes

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