3H-2,1-Benzoxathiol-3-one 1,1-dioxide → HCID 18704500, compound

HRID 1585964Notes

Reaction equation

HRID 1585964 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C:12]([CH2:15][OH:16])([CH3:14])[C:11](=[O:17])[NH:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8].[CH:18]1[CH:23]=[C:22]2[C:24]([O:26][S:27](=[O:29])(=[O:28])[C:21]2=[CH:20][CH:19]=1)=[O:25]>C(#N)C>[S:27]([C:21]1[CH:20]=[CH:19][CH:18]=[CH:23][C:22]=1[C:24]([O:16][CH2:15][C:12]1([CH3:14])[CH2:13][N:9]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=2)[NH:10][C:11]1=[O:17])=[O:25])([OH:29])(=[O:28])=[O:26]

Participants

4

Reactant 2

HCID 657293H-2,1-Benzoxathiol-3-one 1,1-dioxideHCID 18704497HCID 18704497, compound

Product 1

HCID 18704500HCID 18704500, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of {1-(3,4-dimethylphenyl)-4-hydroxymethyl-4-methyl-3-pyrazolidinone (10.0 g, 42.74 mmol) in dry acetonitrile (200 ml), was added 2-sulfobenzoic acid cyclic anhydride (7.86 g, 42.74 mmol) in a single portion at room temperature with stirring. The reaction mixture was heated to reflux under nitrogen for 22 hours until complete dissolution was observed. After cooling the mixture to room temperature, a heavy precipitate formed, which was recovered by filtration with suction. After washing with acetonitrile and drying under vacuum, 13.7 g (77%) of {1-(3,4-dimethylphenyl)-4-methyl-3-oxo-pyrazolidin-4-yl}methyl 2-sulfobenzoate (Compound III) were isolated in the form of a pale pink solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under nitrogen for 22 hours until complete dissolution
  3. customa heavy precipitate formed
  4. filtrationwhich was recovered by filtration with suction
  5. washAfter washing with acetonitrile
  6. customdrying under vacuum

Sources & evidence

ORD record
ord-4e0ecae9068a4ba388a00d5143cc1d00
Source dataset
uspto-grants-1999_08
Patent number
US05942379

Reaction notes

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