Dimethyl Sulfoxide → HCID 19016835, compound

HRID 1681845Notes

Reaction equation

HRID 1681845 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:14](=[O:15])[CH2:13][CH:12]3[CH2:16][CH2:17][S:18][C:19]4[S:23][CH:22]=[CH:21][C:20]=4[C:11]3=[N:10]2)=[CH:5][CH:4]=1.CS(C)=O>Br.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]3[CH2:16][CH2:17][S:18][C:19]4[S:23][CH:22]=[CH:21][C:20]=4[C:11]3=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 19016791HCID 19016791, compound

Product 1

HCID 19016835HCID 19016835, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

To a solution of 14.8 g of 2-(4-methoxyphenyl)-4,4a,5,6-tetrahydrothieno[2',3':2,3]thiepino[4,5-c]-pyridazin-3(2H)-one in 100 ml of 30% hydrogen bromide-acetic acid is added 6.1 ml of dimethylsulfoxide with stirring at room temperature. The mixture is stirred for 4 hours at room temperature, poured into ice-cold water and extracted with chloroform. The extract is washed with water, dried and concentrated under reduced pressure. The resulting crystals are recrystallized from a mixed solvent of toluene and isopropyl ether to give 10 g of 2-(4-methoxyphenyl)-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one as white crystals, melting at 126°-128° C.

Workup

  1. stirringThe mixture is stirred for 4 hours at room temperature
  2. additionpoured into ice-cold water
  3. extractionextracted with chloroform
  4. washThe extract is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crystals are recrystallized from a mixed solvent of toluene and isopropyl ether

Sources & evidence

ORD record
ord-d80ec47b373146cf9cc6421dd22125c3
Source dataset
uspto-grants-1992_12
Patent number
US05175162

Reaction notes

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