Water → HCID 19016811, compound

HRID 1728940Notes

Reaction equation

HRID 1728940 reaction equation
Cl[CH2:2][C:3]([C:5]1[S:26][C:8]2[S:9][CH2:10][CH2:11][C:12]3[C:13](=[N:14][N:15]([C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=4)[C:16](=[O:18])[CH:17]=3)[C:7]=2[CH:6]=1)=[O:4].[C:27]([O-:30])(=[O:29])[CH3:28].[K+].O>C(O)(=O)C>[C:27]([O:30][CH2:2][C:3]([C:5]1[S:26][C:8]2[S:9][CH2:10][CH2:11][C:12]3[C:13](=[N:14][N:15]([C:19]4[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=4)[C:16](=[O:18])[CH:17]=3)[C:7]=2[CH:6]=1)=[O:4])(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 517044Potassium AcetateHCID 19016810HCID 19016810, compound

Product 1

HCID 19016811HCID 19016811, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 3.2 g of 9-chloroacetyl-2-(4-chlorophenyl)-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one obtained in Example 47 in 40 ml of acetic acid is added 6.0 g of potassium acetate and the mixture is refluxed under heating for 3 hours with stirring. After cooling, to the mixture is added water and the solution is extracted with chloroform. The extract is washed with water, dried and concentrated under reduced pressure. The resulting residue is subjected to column chromatography on silica gel and eluted with a mixed solvent of chloroform and methanol (99:1). The crystals obtained from the fraction are recrystallized from a mixed solvent of chloroform and ethanol to give 9-acetyloxyacetyl-2-(4-chlorophenyl)-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one as white crystals, melting at 172°-174° C.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureunder heating for 3 hours
  3. temperatureAfter cooling, to the mixture
  4. extractionthe solution is extracted with chloroform
  5. washThe extract is washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. washeluted with a mixed solvent of chloroform and methanol (99:1)
  9. customThe crystals obtained from the fraction
  10. customare recrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-baee15cb7f1144e3b7aafd0303eb92f0
Source dataset
uspto-grants-1994_07
Patent number
US05329016

Reaction notes

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