3-Amino-5-methyl-4H-1,2,4-triazole → HCID 178469337, compound

HRID 477545

Reaction equation

HRID 477545 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([CH3:7])[NH:4][N:3]=1.[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])#[C:9][C:10]([O-])=[O:11]>C(O)C>[CH2:16]([O:15][C:13]([C:8]1[CH:9]=[C:10]([OH:11])[N:6]2[C:5]([CH3:7])=[N:4][N:3]=[C:2]2[N:1]=1)=[O:14])[CH3:17]

Participants

4

Reactant 2

HCID 2346103-Amino-5-methyl-4H-1,2,4-triazoleHCID 713605752-Butynedioic acid, monoethyl ester

Product 1

HCID 178469337HCID 178469337, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 14.7 g of 3-amino-5-methyl-s-triazole and 26.8 g of ethyl acetylenedicarboxylate in 120 ml of ethanol was refluxed for three hours, the reaction mixture was allowed to stand at room temperature for one hour, and the formed crystals were collected by filtration. The filtrate was concentrated and the residue was recrystallized from dichloromethane, and the crystals were joined with those obtained above. Purification by silica gel chromatography gave 10.8 g of the objective compound as colorless crystals.

Workup

  1. temperaturewas refluxed for three hours
  2. filtrationthe formed crystals were collected by filtration
  3. concentrationThe filtrate was concentrated
  4. customthe residue was recrystallized from dichloromethane
  5. customthose obtained above
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-f2a342a9eb6b4a2bbadb50739037fd98
Source dataset
uspto-grants-1989_12
Patent number
US04888332

Linked notes

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