Cyanoacetamide → HCID 10405941, compound

HRID 280634Notes

Reaction equation

HRID 280634 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].C[O-].[Na+].[Cl:10][C:11]1[CH:28]=[CH:27][C:14]([C:15]([C:17]2[CH:26]=[CH:25][C:20]([CH2:21][N:22]=[N+:23]=[N-:24])=[CH:19][CH:18]=2)=[O:16])=[CH:13][CH:12]=1>C(O)C>[NH2:2][C:1]1[N:22]([CH2:21][C:20]2[CH:19]=[CH:18][C:17]([C:15](=[O:16])[C:14]3[CH:27]=[CH:28][C:11]([Cl:10])=[CH:12][CH:13]=3)=[CH:26][CH:25]=2)[N:23]=[N:24][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 10942334Sodium MethoxideHCID 13649659HCID 13649659, compound

Product 1

HCID 10405941HCID 10405941, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-cyanoacetamide (527 mg, 6.27 mmol) in ethanol (20 ml) was added sodium methoxide (330 mg, 6.11 mmol). The mixture was refluxed 15 minutes, cooled slightly, and 4-(4-chlorobenzoyl)benzyl azide (1.24 g, 4.56 mmol) was added. The mixture was refluxed 2 hours, cooled to ambient temperature, and filtered. The filtrate was evaporated under vacuum and the residue was triturated with hot 19:1 (v/v) dichloromethane-methanol (50 ml) and filtered. The remaining solid was triturated with hot methanol (3 ml), filtered, and dried at 60° C. under vacuum to provide 182 mg (11%) of 5-amino-1-(4-[4-chlorobenzoyl]benzyl)-1,2,3-triazole-4-carboxamide, m.p. 229°-231° C.

Workup

  1. temperatureThe mixture was refluxed 15 minutes
  2. temperaturecooled slightly
  3. temperatureThe mixture was refluxed 2 hours
  4. filtrationfiltered
  5. customThe filtrate was evaporated under vacuum
  6. customthe residue was triturated with hot 19:1 (v/v) dichloromethane-methanol (50 ml)
  7. filtrationfiltered
  8. customThe remaining solid was triturated with hot methanol (3 ml)
  9. filtrationfiltered
  10. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-5ca252c3d6a44f7cb8b8a3c98e8c7129
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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