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

HRID 1447748

Reaction equation

HRID 1447748 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 two 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 two 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-526c9df1962348b5a18969ed43d1a994
Source dataset
uspto-grants-1979_12
Patent number
US04178280

Linked notes

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