Methanesulfonyl chloride → 2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl methanesulfonate

HRID 1859940Notes

Reaction equation

HRID 1859940 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][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]>ClCCl.C(N(CC)CC)C>[CH3:1][S:2]([O:6][CH2:7][CH2:8][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])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 77499N-(2-Hydroxyethyl)phthalimide

Product 1

HCID 186258622-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl methanesulfonateYield 67.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

After methanesulfonyl chloride (12.7 g) was added to a solution of N-(2-hydroxyethyl)phthalimide (19.1 g) in anhydrous dichloromethane (200 ml), triethylamine (20 ml) was added dropwise to the mixture in an ice bath. The mixture was stirred at ambient temperature for 4 hours. At the end of this time the reaction mixture was concentrated under reduced pressure. The residual solid was washed with ethyl acetate and water and then recrystallized from ethyl acetate to afford the desired compound (18.2 g).

Workup

  1. additionwas added dropwise to the mixture in an ice bath
  2. concentrationAt the end of this time the reaction mixture was concentrated under reduced pressure
  3. washThe residual solid was washed with ethyl acetate and water
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-68ef658b092743ee90ebd74af6f51dcd
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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