Cyanoacetamide → 5-Amino-1-(3,4-dichlorobenzyl)-1,2,3-triazole-4-carboxamide

HRID 1194713Notes

Reaction equation

HRID 1194713 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[Na].[Cl:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:12][N:13]=[N+:14]=[N-:15]>C(O)C>[Cl:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:12][N:13]1[C:1]([NH2:2])=[C:3]([C:4]([NH2:6])=[O:5])[N:15]=[N:14]1

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 5360545SodiumHCID 150652184-(Azidomethyl)-1,2-dichlorobenzene

Product 1

HCID 140330335-Amino-1-(3,4-dichlorobenzyl)-1,2,3-triazole-4-carboxamideYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A stirred mixture of 3,4-dichlorobenzyl chloride (12.6 g, 64.5 mmol) and sodium azide (7.0 g, 0.11 mole) in absolute ethanol (70 ml) was refluxed for 4.75 hours, cooled and filtered to provide a solution of 3,4-dichlorobenzyl azide. Separately, 2-cyanoacetamide (5.5 g, 65 mmol) was added to a 35° C. solution of sodium (1.5 g, 65 mmol) in absolute ethanol (125 ml), and to the resulting suspension was added the above azide solution dropwise over 10 minutes. The combined mixtures were refluxed for 1 hour, kept 16 hours at ambient temperature and 1 hour at 5° C., and filtered. The crude product was dried under vacuum, dissolved in boiling ethanol (290 ml), filtered hot, and cooled to 0° C. The solid was collected by filtration and dried under vacuum to provide 12.4 g (67%) of 1-(3,4-dichlorobenzyl)-5-amino-1,2,3-triazole-4-carboxamide, m.p. 221°-222° C.

Workup

  1. temperatureThe combined mixtures were refluxed for 1 hour
  2. filtrationfiltered
  3. dry with materialThe crude product was dried under vacuum
  4. dissolutiondissolved
  5. filtrationfiltered hot
  6. filtrationThe solid was collected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-99f79cfb64e145068d73117291d9d5e3
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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