Water → HCID 59310058, compound

HRID 1512987Notes

Reaction equation

HRID 1512987 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])=[CH:6][C:5]([S:19](Cl)(=O)=O)=[C:4]([O:23][CH3:24])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(OCC)(=O)C>O1CCCC1>[Cl:1][C:2]1[C:7]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])=[CH:6][C:5]([SH:19])=[C:4]([O:23][CH3:24])[CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 59310094HCID 59310094, compound

Product 1

HCID 59310058HCID 59310058, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-chloro-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-methoxy-benzenesulfonyl chloride (0.83 g) in tetrahydrofuran (10 mL) were added triphenylphosphine (1.98 g) and water (1.5 mL), and the mixture was stirred at room temperature overnight. To the reaction mixture were added water and ethyl acetate, and the organic layer was separated. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=1/1) to give the title compound (0.62 g).

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-6f524bde285a40aeaff4afd743b5017c
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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