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

HRID 248820

Reaction equation

HRID 248820 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]([OH:15])=O.S(Cl)([Cl:18])=O>>[CH:8]1[CH:9]=[C:10]2[C:2]([N:3]([CH2:12][C:13]([Cl:18])=[O:15])[C:4](=[O:11])[C:5]2=[CH:6][CH:7]=1)=[O:1]

Participants

3

Reactant 2

HCID 20825N-PhthaloylglycineHCID 24386Thionyl Chloride

Product 1

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

Procedure

A solution of 1,3-dihydro-1,3-dioxo-2H-isoindole-2-acetic acid (7.00 g) and thionyl chloride (12 mL) was stirred at reflux under nitrogen for one hour. The thionyl chloride was distilled from the reaction, and the resulting crude product was further purified by distillation via a kugelrohr apparatus (BUCHI, Flawil, Switzerland). [Bp: 160°-180° C. (oven temperature) at 10 mm Hg.]The yield of the title compound was 6.88 grams (90.2%). The structure of the title compound, and of all of the compounds synthesized in each of the subsequent examples, was confirmed by 1H NMR.

Workup

  1. temperatureat reflux under nitrogen for one hour
  2. distillationThe thionyl chloride was distilled from the reaction
  3. distillationthe resulting crude product was further purified by distillation via a kugelrohr apparatus (BUCHI, Flawil, Switzerland)
  4. customThe structure of the title compound, and of all of the compounds synthesized in each of the subsequent examples

Sources & evidence

ORD record
ord-12dac6c8922c4008ba6739349b85633c
Source dataset
uspto-grants-1993_05
Patent number
US05212169

Linked notes

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