Water → HCID 14098733, compound

HRID 1905378Notes

Reaction equation

HRID 1905378 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][S:16][C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=4[C:10]3=[N:9]2)=[CH:4][CH:3]=1.BrBr.O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]3[CH2:15][S:16][C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=4[C:10]3=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 14098698HCID 14098698, compound

Product 1

HCID 14098733HCID 14098733, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 1.7 g of 2-(4-chlorophenyl)-9-methyl-2,3,4,4a-tetrahydro-5H-(1)benzothiopyrano[4,3-c]pyridazin-3-one in 30 ml of acetic acid is added 1.2 g of bromine dropwise with stirring at 40°-50° C. on a water bath. After the completion of addition, the mixture is stirred at 50° C. for 3 hours and poured into an excess amount of water. The precipitated crystals are collected by filtration and recrystallized from acetic acid to give 0.5 g of 2-(4-chlorophenyl)-9-methyl-2,3-dihydro-5H-(1)benzothiopyrano[4,3-c]pyridazin-3-one, melting at 200°-206° C., as a yellow powder.

Workup

  1. additionAfter the completion of addition
  2. stirringthe mixture is stirred at 50° C. for 3 hours
  3. filtrationThe precipitated crystals are collected by filtration
  4. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-dbe60b57411c4d079ca6b91eb0d4e89b
Source dataset
uspto-grants-1989_06
Patent number
US04843075

Reaction notes

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