Water → 5-amino-1-[(2-chlorophenyl)methyl]-1H-1,2,3-triazole-4-carboxamide

HRID 414082Notes

Reaction equation

HRID 414082 reaction equation
[Na].[C:2]([CH2:4][C:5]([NH2:7])=[O:6])#[N:3].[Cl:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[CH2:11][N:12]=[N+:13]=[N-:14].O>C(O)C>[NH2:3][C:2]1[N:12]([CH2:11][C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=2[Cl:8])[N:13]=[N:14][C:4]=1[C:5]([NH2:7])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 7898CyanoacetamideHCID 5360545SodiumHCID 121946022-Chlorobenzyl azide

Product 1

HCID 28153125-amino-1-[(2-chlorophenyl)methyl]-1H-1,2,3-triazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

23 g (1 mol) of sodium are dissolved in 1 litre of ethyl alcohol and 101 g (1.2 mol) of cyanoacetamide are added thereto. 167.5 g (1 mol) of o-chlorobenzyl azide are added to this suspension at 40°-45° and the whole is heated for 2 hours under reflux. After cooling to 30°, 1000 ml of water are added, the precipitated product is filtered off with suction and then washed several times with warm water. After recrystallisation from dioxan and toluene, 5-amino-1-(o-chlorobenzyl)-1H-1,2,3-triazole-4-carboxamide is obtained in the form of colourless crystals having a melting point of 206°-207°.

Workup

  1. temperaturethe whole is heated for 2 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling to 30°
  4. filtrationthe precipitated product is filtered off with suction
  5. washwashed several times with warm water
  6. customAfter recrystallisation from dioxan and toluene

Sources & evidence

ORD record
ord-de707d2e4cca451d9b2adafc81bfed09
Source dataset
uspto-grants-1988_12
Patent number
US04789680

Reaction notes

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