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

HRID 2414139Notes

Reaction equation

HRID 2414139 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-9d16b44cb7a840c3963c1e2203557daa
Source dataset
uspto-grants-1988_01
Patent number
US04721791

Reaction notes

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