Water → N,N'-bis(phthalimido)oxamide N-methyl-2-pyrrolidone

HRID 866525Notes

Reaction equation

HRID 866525 reaction equation
[C:1]1(=[O:11])[O:6][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].[CH3:20][N:21]1[CH2:25][CH2:24][CH2:23][C:22]1=[O:26].[OH2:27]>C1(C)C=CC=CC=1>[C:22]1(=[O:26])[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:9](=[O:27])[C:10]2=[CH:2][CH:1]=[CH:25][CH:24]=[C:23]12.[CH3:20][N:21]1[CH2:9][CH2:10][CH2:2][C:1]1=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 13387N-methyl-2-pyrrolidoneHCID 13826Oxalic acid, dihydrazide

Product 1

HCID 70604243N,N'-bis(phthalimido)oxamide N-methyl-2-pyrrolidone

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. N-methyl-2-pyrrolidone and 500 ml. toluene were heated at reflux until two moles of water were removed (about 2 hours). The mixture was diluted with benzene 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-N-methyl-2-pyrrolidone 1:2 complex.

Workup

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

Sources & evidence

ORD record
ord-34434331b41849359856eaa07ec63f4e
Source dataset
uspto-grants-1978_07
Patent number
US04100132

Reaction notes

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