Water → HCID 18704493, compound

HRID 2287290Notes

Reaction equation

HRID 2287290 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].O>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

5

Reactant 3

HCID 962WaterHCID 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 neat acetonitrile (200 ml), there is added 2-sulfobenzoic acid cyclic anhydride (8.9 g, 48.5 mmol) all at the same time, at room temperature, while stirring. The reaction mixture is heated to reflux under nitrogen until complete dissolution is observed. The process is continued for 24 hours and the mixture is cooled in a bath of ice and water for 2 hours. A solid precipitant is obtained that is collected by filtration and washed with acetonitrile cooled by means of ice. After drying under vacuum, 17.9 g (95%) of 4-methyl-3-oxo-l-phenyl-pyrazolidin-4-yl)methyl 2-sulfobenzoate (Compound II) is isolated in the form of a whitish solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux under nitrogen until complete dissolution
  3. customA solid precipitant is obtained
  4. filtrationthat is collected by filtration
  5. washwashed with acetonitrile
  6. temperaturecooled by means of ice
  7. dry with materialAfter drying under vacuum, 17.9 g (95%) of 4-methyl-3-oxo-l-phenyl-pyrazolidin-4-yl)methyl 2-sulfobenzoate (Compound II)
  8. customis isolated in the form of a whitish solid

Sources & evidence

ORD record
ord-c2cd6fb775024736aa84c46f1f90b817
Source dataset
uspto-grants-2000_07
Patent number
US06083673

Reaction notes

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