Dimethyl Sulfoxide → HCID 10809204, compound

HRID 235268Notes

Reaction equation

HRID 235268 reaction equation
[C:1]([C:4]1[S:25][C:7]2[CH2:8][CH2:9][CH2:10][CH:11]3[CH2:16][C:15](=[O:17])[N:14]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=4)[N:13]=[C:12]3[C:6]=2[CH:5]=1)(=[O:3])[CH3:2].CS(C)=O.S([O-])(O)=O.[Na+]>Br.C(O)(=O)C>[C:1]([C:4]1[S:25][C:7]2[CH2:8][CH2:9][CH2:10][C:11]3[C:12](=[N:13][N:14]([C:18]4[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=4)[C:15](=[O:17])[CH:16]=3)[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 23353994HCID 23353994, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 10809204HCID 10809204, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

To a solution of 1.2 g of 9-acetyl-2-(4-chlorophenyl)-2,4,4a,5,6,7-hexahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one in 15% hydrogen bromide-acetic acid solution was added 0.23 ml of dimethylsulfoxide at room temperature with stirring. After stirring at the same temperature for 15 minutes, the mixture was poured into 0.5% sodium hydrogensulfite solution and extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was chromatographed on a silica gel column using chloroform as an eluent. The resulting solid was recrystallized from ethanol to give 0.4 g of 9-acetyl-2-(4-chlorophenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one as a white crystal, melting at 164°-166° C.

Workup

  1. stirringAfter stirring at the same temperature for 15 minutes
  2. extractionextracted with chloroform
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a silica gel column
  7. customThe resulting solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-cfb81f8bee5f444282bb18fd756b029a
Source dataset
uspto-grants-1997_01
Patent number
US05597918

Reaction notes

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