Benzenesulfonyl chloride → Benzenesulfonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

HRID 2295523Notes

Reaction equation

HRID 2295523 reaction equation
C(N(CC)CC)C.[OH:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[C:20]1([S:26]([O:8][N:9]2[C:10](=[O:19])[C:11]3=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]3[C:13]2=[O:14])(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 10665N-Hydroxyphthalimide

Product 1

HCID 278068Benzenesulfonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl esterYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dichloromethane (50 ml) solution of triethylamine (3.1 g, 0.0306 mole) was slowly added to a stirred dichloromethane (50 ml) suspension of N-hydroxyphthalimide (5.0 g, 0.0306 mole) and benzenesulfonyl chloride (5.4 g, 0.0306 mole) at ice-bath temperature. The stirred reaction mixture was kept at ambient temperature for about 24 hours. The product was partitioned between dichloromethane and distilled water and the dichloromethane extract was dried with magnesium sulfate. Solvent was removed under reduced pressure and the residue was crystallized with ethyl acetate-n-pentane (2:1 v/v) to give 8.0 g (87%) of colorless crystals; mp 186°; mass spectrum M+ 303 (calcd. M+ 303).

Workup

  1. customThe stirred reaction mixture
  2. customThe product was partitioned between dichloromethane
  3. distillationdistilled water
  4. extractionthe dichloromethane extract
  5. dry with materialwas dried with magnesium sulfate
  6. customSolvent was removed under reduced pressure
  7. customthe residue was crystallized with ethyl acetate-n-pentane (2:1 v/v)

Sources & evidence

ORD record
ord-b2a160e51cd64a32b85e541e02878fda
Source dataset
uspto-grants-1984_01
Patent number
US04425424

Reaction notes

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