N-Phthaloylglycine → 2H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-

HRID 356204Notes

Reaction equation

HRID 356204 reaction equation
[C:1]1(=[O:15])[N:5]([CH2:6][C:7](O)=[O:8])[C:4](=[O:10])[C:3]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:2]12.S(Cl)([Cl:18])=O>>[C:1]1(=[O:15])[N:5]([CH2:6][C:7]([Cl:18])=[O:8])[C:4](=[O:10])[C:3]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:2]12

Participants

3

Reactant 2

HCID 20825N-PhthaloylglycineHCID 24386Thionyl Chloride

Product 1

HCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-Yield 97%

Procedure

A mixture of phthalimidoacetic acid (25.1 g, 0.122 mol) and thionyl chloride (50 mL) was heated for one hour under reflux. The reaction mixture was cooled and, then, concentrated under reduced pressure. The concentrate was recrystallized from dichloromethane-hexane to give 26.4 g (97%) the titled compound, which was used for the subsequent reaction without further purification.

Workup

  1. temperaturewas heated for one hour
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate was recrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-1a1438f8e3c74cd180ecb2baf037f46d
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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