Iodoacetic Acid → 2-[(Iodoacetyl)oxy]-1H-isoindole-1,3(2H)-dione

HRID 1275367Notes

Reaction equation

HRID 1275367 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[I:13][CH2:14][C:15](O)=[O:16].C1CCC(N=C=NC2CCCCC2)CC1>CCOC(C)=O>[I:13][CH2:14][C:15]([O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7])=[O:16]

Participants

5

Reactant 3

HCID 5240Iodoacetic AcidHCID 10665N-HydroxyphthalimideHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 152608682-[(Iodoacetyl)oxy]-1H-isoindole-1,3(2H)-dioneYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-Hydroxyphthalimide (1.4 g, 8.7 mmol), iodoacetic acid (1.6 g, 8.7 mmol) and DCC (1.7 g, 8.7 mmol) were added to dry EtOAc (250 mL), and the mixture was stirred for 5 hours at room temperature. The reaction mixture was then filtered, the filtrate was dried, and the residue was crystallized from ethanol to give a white solid (2.15 g, 75%), m.p. 120° C.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customthe filtrate was dried
  3. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-f5142b0c58b84f69ba202541c99a0e19
Source dataset
uspto-grants-2000_12
Patent number
US06160128

Reaction notes

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