Bromine → HCID 19874054, compound

HRID 465306Notes

Reaction equation

HRID 465306 reaction equation
[Br:1][C:2]1[S:23][C:5]2[CH2:6][CH2:7][CH2:8][CH:9]3[CH2:14][C:13](=[O:15])[N:12]([C:16]4[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=4)[N:11]=[C:10]3[C:4]=2[CH:3]=1.BrBr>C(O)(=O)C>[Br:1][C:2]1[S:23][C:5]2[CH2:6][CH2:7][CH2:8][C:9]3[C:10](=[N:11][N:12]([C:16]4[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=4)[C:13](=[O:15])[CH:14]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 19874049HCID 19874049, compound

Product 1

HCID 19874054HCID 19874054, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 2.5 g of 9-bromo-2-(4-chlorophenyl)-2,4,4a,5,6,7-hexahydro-3H-thieno[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one in 40 ml of acetic acid is added a solution of 1.1 g of bromine in 5 ml of acetic acid with stirring at 40° C. over a period of 10 minutes. The mixture is stirred at 40°-50° C. for 20 minutes and poured into ice-cold water. The precipitated crystals are collected by filtration, washed with water, dissolved in chloroform and subjected to column chromatography on silica gel. The crystals obtained from the fraction which has been eluted with chloroform are recrystallized from a mixed solvent of ethanol and chloroform to give 1.5 g of 9-bromo-2-(4-chlorophenyl)-2,5,6,7-tetrahydro-3H-thieno[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one as white crystals, melting at 143°-144° C.

Workup

  1. stirringThe mixture is stirred at 40°-50° C. for 20 minutes
  2. additionpoured into ice-cold water
  3. filtrationThe precipitated crystals are collected by filtration
  4. washwashed with water
  5. dissolutiondissolved in chloroform
  6. customThe crystals obtained from the fraction which
  7. washhas been eluted with chloroform
  8. customare recrystallized from a mixed solvent of ethanol and chloroform

Sources & evidence

ORD record
ord-948531f6bcf8483fb359ef5a4aa6e6d4
Source dataset
uspto-grants-1992_10
Patent number
US05153194

Reaction notes

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