Sulfuric Acid → HCID 23354000, compound

HRID 235266Notes

Reaction equation

HRID 235266 reaction equation
[OH:1][CH2:2][C:3]1[S:24][C:6]2[CH2:7][CH2:8][CH2:9][C:10]3[C:11](=[N:12][N:13]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=4)[C:14](=[O:16])[CH:15]=3)[C:5]=2[CH:4]=1.S(=O)(=O)(O)O.[C:30](=O)([O-])O.[Na+].C(Cl)(Cl)Cl>CO>[CH3:30][O:1][CH2:2][C:3]1[S:24][C:6]2[CH2:7][CH2:8][CH2:9][C:10]3[C:11](=[N:12][N:13]([C:17]4[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=4)[C:14](=[O:16])[CH:15]=3)[C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 23353984HCID 23353984, compound

Product 1

HCID 23354000HCID 23354000, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 0.75 g of 9-hydroxymethyl-2-(4-methylphenyl)2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one in methanol was added 0.1 ml of conc. sulfuric acid at room temperature and the mixture was refluxed under heating for 3 hours. The mixture was poured into aqueous sodium hydrogen carbonate solution and extraced with chloroform. The extract was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel column using chloroform as an eluent. The solid was recrystallized from a mixed solvent of ethanol and isopropyl ether to give 0.7 g of 9-methoxymethyl-2-(4-methylphenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one as a white powder, melting at 109°-110° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 3 hours
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on a silica gel column
  7. customThe solid was recrystallized from a mixed solvent of ethanol and isopropyl ether

Sources & evidence

ORD record
ord-8e851c478bb04c67816c626385775c7b
Source dataset
uspto-grants-1997_01
Patent number
US05597918

Reaction notes

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