Triethylamine → 2-[1-methyl-2-[(methylsulfonyl)oxy]propyl]-1H-isoindole-1,3(2H)-dione

HRID 478985Notes

Reaction equation

HRID 478985 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH:7]([CH3:21])[CH:8]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[CH3:9].C(N(CC)CC)C>CCOCC>[CH3:9][CH:8]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[CH:7]([O:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 600337Phthalimide, N-(2-hydroxy-3-butyl)-

Product 1

HCID 218952722-[1-methyl-2-[(methylsulfonyl)oxy]propyl]-1H-isoindole-1,3(2H)-dioneYield 82.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methanesulfonyl chloride (9.7 mL, 56 mmol) was added to a solution of 10.5 g (48 mmol) of 2-(2-hydroxy-1-methylpropyl)-1H-isoindole-1,3(2H)-dione (JP 01242569 A2) and 8.1 mL (58 mmol) of triethylamine and the mixture was stirred at room temperature overnight. The mixture was diluted with ether and washed with water and brine. Drying (MgSO4) and removal of solvent gave an oil which slowly solidified. Trituration with hexanes gave 11.8 g of 2-[1-methyl-2-[(methylsulfonyl)oxy]propyl]-1H-isoindole-1,3(2H)-dione as a white solid, mp 67-73° C.

Workup

  1. washwashed with water and brine
  2. customDrying
  3. custom(MgSO4) and removal of solvent
  4. customgave an oil which

Sources & evidence

ORD record
ord-74bbd959dc1c480caca4ece9e6a25bd3
Source dataset
uspto-grants-2003_11
Patent number
US06642392B1

Reaction notes

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