Hydrogen Bromide → HCID 19016792, compound

HRID 1728942Notes

Reaction equation

HRID 1728942 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]pyridazin-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-9d60fcc725564f7b833e77b49d24be6c
Source dataset
uspto-grants-1994_07
Patent number
US05329016

Reaction notes

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