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

HRID 1194718Notes

Reaction equation

HRID 1194718 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 32.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A stirred suspension of 2-cyanoacetamide (790 mg, 9.40 mmol) in absolute ethanol (40 ml) was treated with sodium methoxide (495 mg, 9.16 mmol) and refluxed 10 minutes. The mixture was cooled slightly, a solution of 4-chloro-3-cyanobenzyl azide (1.35 g, 7.01 mmol) in absolute ethanol (10 ml) was added in one portion, and the mixture was refluxed 2.5 hours. The mixture was filtered hot, the solid was washed with absolute ethanol, and the combined filtrate and wash were evaporated to dryness under vacuum. The residue was triturated with diethyl ether, filtered, and washed twice with diethyl ether. The solid was recrystallized from methanol (6 ml) and dried at 65° C. under vacuum to provide 635 mg (24%) 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 slightly
  3. temperaturethe mixture was refluxed 2.5 hours
  4. filtrationThe mixture was filtered hot
  5. washthe solid was washed with absolute ethanol
  6. washthe combined filtrate and wash
  7. customwere evaporated to dryness under vacuum
  8. customThe residue was triturated with diethyl ether
  9. filtrationfiltered
  10. washwashed twice with diethyl ether
  11. customThe solid was recrystallized from methanol (6 ml)
  12. customdried at 65° C. under vacuum

Sources & evidence

ORD record
ord-30eebdbcba7545109cb966db5fac197d
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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