Cyanoacetamide → Carboxyamidotriazole

HRID 280653Notes

Reaction equation

HRID 280653 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].C[O-].[Na+].[Cl:10][C:11]1[CH:30]=[CH:29][C:14]([C:15]([C:17]2[C:26]([Cl:27])=[CH:25][C:20]([CH2:21][N:22]=[N+:23]=[N-:24])=[CH:19][C:18]=2[Cl:28])=[O:16])=[CH:13][CH:12]=1>C(O)C>[NH2:2][C:1]1[N:22]([CH2:21][C:20]2[CH:19]=[C:18]([Cl:28])[C:17]([C:15](=[O:16])[C:14]3[CH:29]=[CH:30][C:11]([Cl:10])=[CH:12][CH:13]=3)=[C:26]([Cl:27])[CH:25]=2)[N:23]=[N:24][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 10942334Sodium MethoxideHCID 136496623,5-Dichloro-4-(4-chlorobenzoyl)benzyl azide

Product 1

HCID 108144CarboxyamidotriazoleYield 41.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-cyanoacetamide (149 mg, 1.77 mmol) in ethanol (5 ml) was refluxed 20 minutes with sodium methoxide (93 mg, 1.72 mmol), cooled slightly, treated with 4-(4-chlorobenzoyl)-3,5-dichlorobenzyl azide (450 mg, 1.32 mmol), and refluxed 1 hour. The mixture was cooled, evaporated under vacuum, and chromatographed on a column of silica gel (50 g), eluted with 19:1 (v/v) dichloromethane-methanol to provide 231 mg (41%) of 5-amino-1(4-[4-chlorobenzoyl]-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide, m.p. 198.5°-200° C.

Workup

  1. temperaturecooled slightly
  2. temperaturerefluxed 1 hour
  3. temperatureThe mixture was cooled
  4. customevaporated under vacuum
  5. customchromatographed on a column of silica gel (50 g)
  6. washeluted with 19:1 (v/v) dichloromethane-methanol

Sources & evidence

ORD record
ord-da9711036eb74da8821859fad7300064
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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