Hydrochloric Acid → 4-Hexyl-1,2,4-triazolidine-3,5-dione

HRID 2296384

Reaction equation

HRID 2296384 reaction equation
[C:1]([NH:4][NH:5][C:6]([NH2:8])=[O:7])(N)=[O:2].[CH2:9](N)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Cl>CN1CCCC1=O>[CH2:9]([N:8]1[C:6](=[O:7])[NH:5][NH:4][C:1]1=[O:2])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 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 hydrazodicarbonamide and 56 g of n-hexylamine are stirred in 100 ml of N-methy pyrrolidone for 6 hours at 150° C., for 20 hours at 175° C. and for 20 hours at 180° C. The solvent is then distilled off in vacuo and the residue is triturated with 100 ml of 10% sodium hydroxide solution. The deposit is isolated by filtration under suction and the filtrate is neutralised with 10% hydrochloric acid. A deposit is precipitated and is isolated by filtration under suction, washed with water and dried in vacuo, giving 75 g (81% of the theoretical yield) of 4-(n-hexyl)-1,2,4-triazolidine-3,5-dione in the form of colourless crystals melting at 144° C. to 145° C.

Workup

  1. distillationThe solvent is then distilled off in vacuo
  2. customthe residue is triturated with 100 ml of 10% sodium hydroxide solution
  3. customThe deposit is isolated by filtration under suction
  4. customA deposit is precipitated
  5. customis isolated by filtration under suction
  6. washwashed with water
  7. customdried in vacuo
  8. customgiving 75 g (81% of the

Sources & evidence

ORD record
ord-e983ca716a2840219f9398b2e6ee80f2
Source dataset
uspto-grants-1984_01
Patent number
US04429135

Linked notes

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