Acetone → 10-chloro-2-(4-chlorophenyl)-5,6-dihydro-[1]benzothiepino[5,4-c]-pyridazin-3(2H)-one 7-oxide

HRID 231782Notes

Reaction equation

HRID 231782 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:16][CH2:15][CH2:14][C:13]3[C:8](=[N:9][N:10]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=4)[C:11](=[O:17])[CH:12]=3)[C:6]=2[CH:7]=1.CC(C)=[O:27].O.O.O.Br[O-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:16](=[O:27])[CH2:15][CH2:14][C:13]3[C:8](=[N:9][N:10]([C:18]4[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=4)[C:11](=[O:17])[CH:12]=3)[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 1457889410-chloro-2-(4-chlorophenyl)-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3(2H)-oneHCID 86743234Sodium hypobromite trihydrate

Product 1

HCID 1457891410-chloro-2-(4-chlorophenyl)-5,6-dihydro-[1]benzothiepino[5,4-c]-pyridazin-3(2H)-one 7-oxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2.4 g of 10-chloro-2-(4-chlorophenyl)-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3(2H)-one, prepared in Example 11 in 25 ml of water and 300 ml of acetone is added 2.8 g of sodium hypobromite trihydrate. The mixture is stirred for 18 hours at room temperature and concentrated under reduced pressure. To the residue is added water, the precipitated crystals are collected by filtration and recrystallized from dimethylformamide-water to give 1.0 g of 10-chloro-2-(4-chlorophenyl)-5,6-dihydro-[1]benzothiepino[5,4-c]-pyridazin-3(2H)-one 7-oxide, melting at 239°-241° C. with decomposition.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue is added water
  3. filtrationthe precipitated crystals are collected by filtration
  4. customrecrystallized from dimethylformamide-water

Sources & evidence

ORD record
ord-050302cd8091416cb3b7ddf1b16a8ce9
Source dataset
uspto-grants-1989_07
Patent number
US04849421

Reaction notes

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