Water → HCID 10570553, compound

HRID 1681829Notes

Reaction equation

HRID 1681829 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH2:12][CH:11]3[CH2:15][CH2:16][S:17][C:18]4[S:22][C:21]([CH3:23])=[CH:20][C:19]=4[C:10]3=[N:9]2)=[CH:4][CH:3]=1.BrBr.O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]3[CH2:15][CH2:16][S:17][C:18]4[S:22][C:21]([CH3:23])=[CH:20][C:19]=4[C:10]3=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 10761180HCID 10761180, compound

Product 1

HCID 10570553HCID 10570553, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 3.6 g of 2-(4-chlorophenyl)-9-methyl-4,4a,5,6-tetrahydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one in 50 ml of acetic acid is added dropwise a solution of 1.7 g of bromine in 15 ml of acetic acid stirring for 15 minutes at 40°-45° C. The mixture is stirred for 20 minutes at the same temperature and then poured into 200 ml of water. The precipitated crystals are collected by filtration and washed with water. The resulting crystals are subjected to column chromatography on silica gel and eluted with chloroform. The crystals obtained from the fraction are recrystallized from a mixed solvent of chloroform and ethanol to give 2.2 g of 2-(4-chlorophenyl)-9-methyl-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one as pale brown crystals, melting at 150°-151° C.

Workup

  1. filtrationThe precipitated crystals are collected by filtration
  2. washwashed with water
  3. washeluted with chloroform
  4. customThe crystals obtained from the fraction
  5. customare recrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-6810568fac0647df946cf6d22e22fca3
Source dataset
uspto-grants-1992_12
Patent number
US05175162

Reaction notes

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