Cyanoacetamide → Carboxyamidotriazole

HRID 1403797Notes

Reaction equation

HRID 1403797 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:21])[C:11]=1[C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[CH2:5][N:6]=[N+:7]=[N-:8].[C:22]([CH2:24][C:25]([NH2:27])=[O:26])#[N:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH2:23][C:22]1[N:6]([CH2:5][C:4]2[CH:3]=[C:2]([Cl:1])[C:11]([C:12](=[O:20])[C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)=[C:10]([Cl:21])[CH:9]=2)[N:7]=[N:8][C:24]=1[C:25]([NH2:27])=[O:26]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 11430Potassium CarbonateHCID 136496623,5-Dichloro-4-(4-chlorobenzoyl)benzyl azide

Product 1

HCID 108144Carboxyamidotriazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,5-dichloro-4-(4′-chlorobenzoyl)benzyl azide (858.D) (1 mole) is reacted with cyanoacetamide (1.69 mole) in hot Acetonitrile, and Potassium carbonate, (6.2 mole) to give 5-amino-1-(4-(4-chlorobenzoyl)-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide (858.E).

Sources & evidence

ORD record
ord-df4d317c4dbf4934bce799cb347bb970
Source dataset
uspto-grants-2014_12
Patent number
US08912223B2

Reaction notes

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