Water → HCID 10831201, compound

HRID 465305Notes

Reaction equation

HRID 465305 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][CH2:17][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][CH2:17][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 10521420HCID 10521420, compound

Product 1

HCID 10831201HCID 10831201, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3.6 g of 2-(4-chlorophenyl)-9-methyl-2,4,4a,5,6,7-hexahydro-3H-thieno[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one in 30 ml of acetic acid is added 0.6 ml of bromine at 40° C. with stirring and the reaction mixture is stirred at 40-45° C. for 30 minutes. The mixture is poured into water and the resultant oil is collected by decantation. The crude product is subjected to column chromatography on silica gel and eluted with chloroform to give 1.27 g of 2-(4-chlorophenyl)-2,5,6,7-tetrahydro-9-methyl-3H-thieno[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one, melting at 149.5°-151° C.

Workup

  1. stirringthe reaction mixture is stirred at 40-45° C. for 30 minutes
  2. customthe resultant oil is collected by decantation
  3. washeluted with chloroform

Sources & evidence

ORD record
ord-aecabc76988c416db077c28be28f0f25
Source dataset
uspto-grants-1992_10
Patent number
US05153194

Reaction notes

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