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

HRID 866526

Reaction equation

HRID 866526 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].CS(C)=O.[OH2:24]>C1(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:24])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]12

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 6811Phthalic AnhydrideHCID 13826Oxalic acid, dihydrazide

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Two moles of phthalic anhydride (296 g.) and one mole of oxalic dihydrazide (118 g.) in 500 ml. dimethyl sulfoxide and 750 ml. toluene were heated at reflux until two moles of water were removed (about 2 hours). The mixture was cooled and filtered. After washing with benzene, the white product was dried to constant weight at 50° C giving an essentially quantitative yield of N,N'bis(phthalimido)oxamide #-# dimethyl sulfoxide 1:2 complex.

Workup

  1. customwere removed (about 2 hours)
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washAfter washing with benzene
  5. customthe white product was dried to constant weight at 50° C

Sources & evidence

ORD record
ord-6df4c634f5fb4287861990b6ed1ce0ee
Source dataset
uspto-grants-1978_07
Patent number
US04100132

Linked notes

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