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

HRID 1709666Notes

Reaction equation

HRID 1709666 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].C[O-].[Na+].[Cl:10][C:11]1[CH:20]=[CH:19][C:14]([CH2:15][N:16]=[N+:17]=[N-:18])=[CH:13][C:12]=1[C:21]#[N:22]>C(O)C>[NH2:2][C:1]1[N:16]([CH2:15][C:14]2[CH:19]=[CH:20][C:11]([Cl:10])=[C:12]([C:21]#[N:22])[CH:13]=2)[N:17]=[N:18][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 10942334Sodium MethoxideHCID 230362384-Chloro-3-cyanobenzyl azide

Product 1

HCID 140330325-Amino-1-(4-chloro-3-cyanobenzyl)-1,2,3-triazole-4-carboxamideYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A stirred suspension of 2-cyanoacetamide (790 mg, 9.4 mmol) in absolute ethanol (40 ml) was treated with sodium methoxide (495 mg, 9.2 mmol) and refluxed 10 minutes. The mixture was cooled lightly, a solution of 4-chloro-3-cyanobenzyl azide (1.35 g, 7.0 mmol) in absolute ethanol was added, and the mixture was refluxed 2.5 hours. The mixture was filtered hot and the filtrate evaporated under vacuum. The residue was triturated with diethyl ether, filtered, and washed twice with diethyl ether. The solid was crystallized from refluxing methanol, filtered, washed twice with methanol and once with diethyl ether, and dried at 65° C. under vacuum to provide 635 mg (33%) 5-amino-1-(4-chloro-3-cyanobenzyl)-1,2,3-triazole-4-carboxamide, m.p. 172°-175° C.

Workup

  1. temperaturerefluxed 10 minutes
  2. temperatureThe mixture was cooled lightly
  3. temperaturethe mixture was refluxed 2.5 hours
  4. filtrationThe mixture was filtered hot
  5. customthe filtrate evaporated under vacuum
  6. customThe residue was triturated with diethyl ether
  7. filtrationfiltered
  8. washwashed twice with diethyl ether
  9. customThe solid was crystallized
  10. temperaturefrom refluxing methanol
  11. filtrationfiltered
  12. washwashed twice with methanol and once with diethyl ether
  13. customdried at 65° C. under vacuum

Sources & evidence

ORD record
ord-5716ec6b46de438f85be8913f340dac4
Source dataset
uspto-grants-1990_08
Patent number
US04950673

Reaction notes

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