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

HRID 2296386Notes

Reaction equation

HRID 2296386 reaction equation
[C:1]([NH:4][NH:5][C:6]([NH2:8])=[O:7])(N)=[O:2].[CH:9]1(N)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.Cl>CN1CCCC1=O>[CH:9]1([N:8]2[C:6](=[O:7])[NH:5][NH:4][C:1]2=[O:2])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7965CyclohexylamineHCID 80391,2-Hydrazinedicarboxamide

Product 1

HCID 112638834-cyclohexyl-1,2,4-triazolidine-3,5-dione

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

118 g of hydrazodicarbonamide and 100 g of cyclohexyl amine are stirred in 100 ml of N-methyl pyrrolidone for 2 hours at 160° C., for 7 hours at 175° C. and for 10 hours at 200° C. The solvent is then distilled off in vacuo and the residue is triturated with 100 ml of a 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 132 g (76% of the theoretical yield) of 4-cyclohexyl-1,2,4-triazolidine-3,5-dione (identical with the compounds produced in accordance with Example 2).

Workup

  1. distillationThe solvent is then distilled off in vacuo
  2. customthe residue is triturated with 100 ml of a 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 132 g (76% of the

Sources & evidence

ORD record
ord-56b3b84d9131429fa6176953d2e8a705
Source dataset
uspto-grants-1984_01
Patent number
US04429135

Reaction notes

Loading…