Thionyl Chloride → 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-methyl-propionyl chloride

HRID 1612374Notes

Reaction equation

HRID 1612374 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]([N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])([CH3:10])[C:7](O)=[O:8]>>[CH3:5][C:6]([N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])([CH3:10])[C:7]([Cl:3])=[O:8]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 7743691,3-Dihydro-α,α-dimethyl-1,3-dioxo-2H-isoindole-2-acetic acid

Product 1

HCID 222533222-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-methyl-propionyl chlorideYield 98.3%

Procedure

Thionyl chloride (750 ml, 10.28 mol) was added to 2-methyl-2-phthalimidopropanoic acid (385 g, 1.65 mol) and the mixture refluxed under nitrogen for 3 hours. Excess thionyl chloride was removed under reduced pressure to yield a solid. The solid was washed with diethyl ether (2×250 ml) to yield the title compound as a white crystalline solid (408.2 g, 98%).

Workup

  1. temperaturethe mixture refluxed under nitrogen for 3 hours
  2. customExcess thionyl chloride was removed under reduced pressure
  3. customto yield a solid
  4. washThe solid was washed with diethyl ether (2×250 ml)

Sources & evidence

ORD record
ord-7001b59a8c114939800b4dc7f32e6763
Source dataset
uspto-grants-2006_01
Patent number
US06992184B2

Reaction notes

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