3H-2,1-Benzoxathiol-3-one 1,1-dioxide → HCID 18704493, compound

HRID 1585963Notes

Reaction equation

HRID 1585963 reaction equation
[CH3:1][C:2]1([CH2:14][OH:15])[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][C:3]1=[O:13].[CH:16]1[CH:21]=[C:20]2[C:22]([O:24][S:25](=[O:27])(=[O:26])[C:19]2=[CH:18][CH:17]=1)=[O:23]>C(#N)C>[S:25]([C:19]1[CH:18]=[CH:17][CH:16]=[CH:21][C:20]=1[C:22]([O:15][CH2:14][C:2]1([CH3:1])[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][C:3]1=[O:13])=[O:23])([OH:27])(=[O:26])=[O:24]

Participants

4

Reactant 2

HCID 657293H-2,1-Benzoxathiol-3-one 1,1-dioxideHCID 922384-(Hydroxymethyl)-4-methyl-1-phenylpyrazolidin-3-one

Product 1

HCID 18704493HCID 18704493, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 4-methyl-4-hydroxymethyl-1-phenyl-3-pyrazolidinone (dimezone-S) (10 g, 48.5 mmol) in dry acetonitrile (200 ml), was added 2-sulfobenzoic acid cyclic anhydride (8.9 g, 48.5 mmol) in a single portion at room temperature with stirring. The reaction mixture was heated to reflux under nitrogen until complete dissolution was observed. The reflux was continued for 24 hours and the mixture was cooled in an ice/water bath for 2 hours. A solid precipitate was obtained which was recovered by filtration and washed with ice cooled acetonitrile. After drying under vacuum, 17.9 g (95%) of 4-methyl-3-oxo-1-phenyl-pyrazolidin-4-yl)methyl 2-sulfobenzoate (Compound II) were isolated as an off-white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under nitrogen until complete dissolution
  3. temperaturethe mixture was cooled in an ice/water bath for 2 hours
  4. customA solid precipitate was obtained which
  5. filtrationwas recovered by filtration
  6. washwashed with ice
  7. temperaturecooled acetonitrile
  8. dry with materialAfter drying under vacuum, 17.9 g (95%) of 4-methyl-3-oxo-1-phenyl-pyrazolidin-4-yl)methyl 2-sulfobenzoate (Compound II)
  9. customwere isolated as an off-white solid

Sources & evidence

ORD record
ord-04da466a4d194b7b8947ec003ac9d0ee
Source dataset
uspto-grants-1999_08
Patent number
US05942379

Reaction notes

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