Hydrogen Bromide → HCID 19016792, compound

HRID 1681844Notes

Reaction equation

HRID 1681844 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[S:21][C:20]([CH2:22][CH3:23])=[CH:19][C:18]=4[C:10]3=[N:9]2)=[CH:4][CH:3]=1.Br.CS(C)=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[S:21][C:20]([CH2:22][CH3:23])=[CH:19][C:18]=4[C:10]3=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 19016834HCID 19016834, compound

Product 1

HCID 19016792HCID 19016792, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5 g of 2-(4-chlorophenyl)-8-ethyl-4a,5-dihydro-2H-thieno[2',3':2,3]thiopyrano[4,5-c]pyridazin-3(4H)-one in a 30% solution of hydrogen bromide in acetic acid is added 2 ml of dimethylsulfoxide at room temperature. After the mixture is stirred for an hour at the same temperature, the mixture is poured into ice-cold water and extracted with chloroform. The extract is washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The resulting crystals are recrystallized from a mixed solvent of chloroform and ethanol to give 3.5 g of 2-(4-chlorophenyl)-8-ethyl-5H-thieno[2',3':2,3]thiopyrano[4,5-c]pyridazine-3(2H)-one as yellow needles, melting at 161°-163° C.

Workup

  1. additionthe mixture is poured into ice-cold water
  2. extractionextracted with chloroform
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crystals are recrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-7502e7aa52a24771b572b6221e5b5454
Source dataset
uspto-grants-1992_12
Patent number
US05175162

Reaction notes

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