2-Sulfobenzoic acid cyclic anhydride → HCID 18704498, compound

HRID 1585965Notes

Reaction equation

HRID 1585965 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]2[CH2:15][C:14]([CH2:17][OH:18])([CH3:16])[C:13](=[O:19])[NH:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH:20]1[CH:25]=[C:24]2[C:26]([O:28][S:29](=[O:31])(=[O:30])[C:23]2=[CH:22][CH:21]=1)=[O:27]>O1CCCC1>[S:29]([C:23]1[CH:22]=[CH:21][CH:20]=[CH:25][C:24]=1[C:26]([O:18][CH2:17][C:14]1([CH3:16])[CH2:15][N:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:12][C:13]1=[O:19])=[O:27])([OH:31])(=[O:30])=[O:28]

Participants

4

Reactant 2

HCID 657292-Sulfobenzoic acid cyclic anhydrideHCID 18704496HCID 18704496, compound

Product 1

HCID 18704498HCID 18704498, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of {1-(3,4-dimethoxyphenyl)-4-hydroxymethyl-4-methyl-3-pyrazolidinone (1.0 g, 3.76 mmol) in dry tetrahydrofuran (20 ml) was added 2-sulfobenzoic acid cyclic anhydride (0.69 g, 3.76 mmol), in a single portion at room temperature with stirring. The reaction medium was heated to reflux under nitrogen for 24 hours until complete dissolution was observed. The mixture was cooled in a ice/water bath and the solid was recovered by filtration and washed with acetonitrile. After drying under vacuum, 0.93 g (55%) of {1-(3,4-dimethoxyphenyl)-4-methyl-3-oxo-pyrazolidin-4-yl}methyl 2-sulfobenzoate (Compound IV) was isolated in the form of a pale yellow solid.

Workup

  1. temperatureThe reaction medium was heated
  2. temperatureto reflux under nitrogen for 24 hours until complete dissolution
  3. temperatureThe mixture was cooled in a ice/water bath
  4. filtrationthe solid was recovered by filtration
  5. washwashed with acetonitrile
  6. customAfter drying under vacuum

Sources & evidence

ORD record
ord-f25b48dc3022425e9461552b3e81a0ae
Source dataset
uspto-grants-1999_08
Patent number
US05942379

Reaction notes

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