1,2-Hydrazinedicarboxamide → 4-Hexyl-1,2,4-triazolidine-3,5-dione

HRID 1388758Notes

Reaction equation

HRID 1388758 reaction equation
[NH:1]([C:6]([NH2:8])=[O:7])[NH:2][C:3](N)=[O:4].[CH2:9](N)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>CN1CCCC1=O>[CH2:9]([N:8]1[C:3](=[O:4])[NH:2][NH:1][C:6]1=[O:7])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 80391,2-HydrazinedicarboxamideHCID 8102Hexylamine

Product 1

HCID 204701154-Hexyl-1,2,4-triazolidine-3,5-dione

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

60 g of hydrazodicarboxamide and 56 g of n-hexylamine in 100 ml of N-methylpyrrolidone are stirred at 150° C. for 6 hours, at 175° C. for 20 hours and at 180° C. for 20 hours. The solvent is then distilled off in vacuo and the residue is triturated with 100 ml of 10% strength sodium hyroxide solution. The precipitate is filtered off and the filtrate is neutralised with 10% strength hydrochloric acid. A precipitate thereby separates out, and is filtered off, washed with water and dried in vacuo. 75 g (81% of the theoretical yield) of 4-(n-hexyl)-1,2,4-triazolidine-3,5-dione are obtained as colourless crystals of melting point 144°-145° C.

Workup

  1. distillationThe solvent is then distilled off in vacuo
  2. customthe residue is triturated with 100 ml of 10% strength sodium hyroxide solution
  3. filtrationThe precipitate is filtered off
  4. filtrationis filtered off
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-ff650ae96fe9437bb052d463314aaba6
Source dataset
uspto-grants-1984_02
Patent number
US04433085

Reaction notes

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