Acetone → N-hydroxyphthalimide p-styrenesulfonate

HRID 359668Notes

Reaction equation

HRID 359668 reaction equation
CC(C)=[O:3].[OH:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].[CH2:17]=[CH:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(N(CC)CC)C>[OH:5][N:6]1[C:7](=[O:16])[C:8]2=[CH:15][CH:14]=[CH:13][CH:12]=[C:9]2[C:10]1=[O:11].[CH2:17]=[CH:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O-:27])(=[O:3])=[O:26])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 10665N-HydroxyphthalimideHCID 9855777Styrene-4-sulfonyl chloride

Product 1

HCID 86744680N-hydroxyphthalimide p-styrenesulfonate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

50 ml of acetone was added to 3.3 g of N-hydroxyphthalimide and 4.1 g of p-styrenesulfonyl chloride. 2.0 g of triethylamine was dropwise added to the mixture under stirring at room temperature (about 20° C.). The mixture was stirred at room temperature for additional 1 hr. and poured into 200 g of ice/water. The precipitate thus formed was recrystallized from a solvent mixture of benzene/ethanol to obtain 4.6 g of N-hydroxyphthalimide-p-styrenesulfonate.

Workup

  1. stirringThe mixture was stirred at room temperature for additional 1 hr
  2. customThe precipitate thus formed
  3. customwas recrystallized from a solvent mixture of benzene/ethanol

Sources & evidence

ORD record
ord-321a38b9ad114586a6e7e351f26047bd
Source dataset
uspto-grants-1991_03
Patent number
US05002853

Reaction notes

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