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

HRID 231781Notes

Reaction equation

HRID 231781 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:16][CH2:15][CH2:14][CH: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])[CH2:12]3)[C:6]=2[CH:7]=1.BrBr>C(O)(=O)C>[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: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

4

Reactant 2

HCID 24408BromineHCID 1457888410-chloro-2-(4-chlorophenyl)-4,4a,5,6,-tetrahydro-[1]benzothiepino[5,4-c]pyridazin-3(2H)-one

Product 1

HCID 1457889410-chloro-2-(4-chlorophenyl)-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3(2H)-oneYield 80.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 3.0 g of 10-chloro-2-(4-chlorophenyl)-4,4a,5,6,-tetrahydro-[1]benzothiepino[5,4-c]pyridazin-3(2H)-one obtained in Example 10 in 90 ml of acetic acid is added 0.4 ml of bromine at 40°-50° C. and stirred for 30 minutes at the same temperature. The mixture is concentrated under reduced pressure and to the residue is added water. The precipitated crystals are collected by filtration, dissolved in chloroform and the solution is washed with water. The organic layer is dried over anhydrous magnesium sulfate and the solvent is distilled off. The crude product obtained is purified by column chromatography and recrystallized from chloroformmethanol to give 2.4 g of 10-chloro-2-(4-chlorophenyl)-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3(2H)-one, melting at 215°-217° C.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure and to the residue
  2. additionis added water
  3. filtrationThe precipitated crystals are collected by filtration
  4. dissolutiondissolved in chloroform
  5. washthe solution is washed with water
  6. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off
  8. customThe crude product obtained
  9. customis purified by column chromatography
  10. customrecrystallized from chloroformmethanol

Sources & evidence

ORD record
ord-d008c32b6e8a4a9b85ac84f18ec8dbea
Source dataset
uspto-grants-1989_07
Patent number
US04849421

Reaction notes

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