Water → Ethanediamide, N1,N2-bis(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-

HRID 866523

Reaction equation

HRID 866523 reaction equation
[C:1]1(=[O:11])O[C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12]([NH:18][NH2:19])(=[O:17])[C:13]([NH:15][NH2:16])=[O:14].[OH2:20]>C1(C)C(C)=CC=CC=1>[C:4]1(=[O:5])[N:16]([NH:15][C:13]([C:12]([NH:18][N:19]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:5])=[O:17])=[O:14])[C:1](=[O:20])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]12

Participants

5

Reactant 3

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 13826Oxalic acid, dihydrazide

Product 1

HCID 113193Ethanediamide, N1,N2-bis(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-Yield 94%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Two moles of phthalic anhydride (296g) and one mole of oxalic dihydrazide (118 g) in xylene (2.5 l) were heated at reflux until two moles of water were removed (about 24 hours). The product was filtered and dried at 50° C. N,N'-bis(phthalimido)-oxamide was obtained in 94-6 percent yield. The compound was a white solid melting at 295° C (dec.) and having the following elemental analysis by weight percent:

Workup

  1. customwere removed (about 24 hours)
  2. filtrationThe product was filtered
  3. customdried at 50° C

Sources & evidence

ORD record
ord-b37e282ca629479f922fa055cd857357
Source dataset
uspto-grants-1978_07
Patent number
US04100132

Linked notes

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