1,2-Hydrazinedicarboxamide → 4-[[3-[(3,5-Dioxo-1,2,4-triazolidin-4-yl)methyl]phenyl]methyl]-1,2,4-triazolidine-3,5-dione

HRID 851794

Reaction equation

HRID 851794 reaction equation
[C:1]([NH:4][NH:5][C:6]([NH2:8])=[O:7])(N)=[O:2].[C:9]1([CH2:17][NH2:18])[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15]N)[CH:10]=1>CN1CCCC1=O>[NH:5]1[C:6](=[O:7])[N:8]([CH2:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([CH2:17][N:18]3[C:6](=[O:7])[NH:5][NH:4][C:1]3=[O:2])[CH:10]=2)[C:1](=[O:2])[NH:4]1

Participants

4

Reactant 2

HCID 80391,2-HydrazinedicarboxamideHCID 151331,3-Benzenedimethanamine

Product 1

HCID 3923254-[[3-[(3,5-Dioxo-1,2,4-triazolidin-4-yl)methyl]phenyl]methyl]-1,2,4-triazolidine-3,5-dione

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

64.2 g of hydrazodicarbonamide and 37 g of m-xylylene diamine in 300 ml of N-methyl pyrrolidone are heated with stirring for 4 hours to 175° C. and for 30 hours to 200° C. The solvent is then distilled off in vacuo and the residue is recrystallised from chloroform, giving 58 g (70% of the theoretical) of 1,3-bis-(1,2,4-triazolidine-3,5-dione-4-yl-methyl)-benzene in the form of colourless crystals melting at 244° to 246° C.

Workup

  1. distillationThe solvent is then distilled off in vacuo
  2. customthe residue is recrystallised from chloroform

Sources & evidence

ORD record
ord-17252b5a382643cc9e601e4bda299810
Source dataset
uspto-grants-1983_05
Patent number
US04386213

Linked notes

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