Methylamine → 2,4-Dihydro-4-methyl-5-propoxy-3H-1,2,4-triazol-3-one

HRID 843295Notes

Reaction equation

HRID 843295 reaction equation
[CH2:1]([O:4][C:5](OCCC)=[N:6][NH:7][C:8]([O:10]C)=O)[CH2:2][CH3:3].[CH3:16][NH2:17]>CO>[CH2:1]([O:4][C:5]1[N:17]([CH3:16])[C:8](=[O:10])[NH:7][N:6]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22617107HCID 22617107, compound

Product 1

HCID 113210922,4-Dihydro-4-methyl-5-propoxy-3H-1,2,4-triazol-3-oneYield 93.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In an autoclave, 10.02 g (44.3 mmol) of methyl N′-dipropoxymethylenehydrazinecarboxylate, 3.94 g of 39% strength solution of methylamine (49.9 mmol) in methanol and 46 g of methanol were initially charged. After 3 hours at 150° C., the solvent was distilled off. The crude substance was taken up in water (20 ml) and extracted repeatedly with methylene chloride. The organic solution was concentrated, giving 6.48 g of 5-propoxy-4-methyl-2,4-dihydro-1,2,4-triazol-3-one with a content of 50%, which corresponds to a yield of 46%.

Workup

  1. distillationthe solvent was distilled off
  2. extractionextracted repeatedly with methylene chloride
  3. concentrationThe organic solution was concentrated

Sources & evidence

ORD record
ord-8f9ea07b7863403ab1ca0e5094037949
Source dataset
uspto-grants-2002_04
Patent number
US06376699B1

Reaction notes

Loading…