Ethyl cyanoacetate → Ethyl 5-amino-1-(4-chlorophenyl)-1H-1,2,3-triazole-4-carboxylate

HRID 27692Notes

Reaction equation

HRID 27692 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[N+:9]=[N-:10])=[CH:4][CH:3]=1.[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12]>C(O)C>[NH2:12][C:11]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=[N:10][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 76803Benzene, 1-azido-4-chloro-

Product 1

HCID 7464933Ethyl 5-amino-1-(4-chlorophenyl)-1H-1,2,3-triazole-4-carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reaction of p-chlorophenyl azide (7.48 g; 0.0487 mole) with ethyl cyanoacetate (5.5 g; 0.0487 mole) as described in example 1a gave 10.057 g (81%) of the triazole of mp (ethanol) 162-164° C. (lit mp 165-167° C.; Ger Offen No. 2,009,134[1970]) (Found; C, 49.78; H, 4.31; N, 21.15; C11H11CIN4O2 requires; C, 49.54; H, 4.16; N, 21.01%).

Sources & evidence

ORD record
ord-d1a01ff221374062814e0eb641624c6c
Source dataset
uspto-grants-1980_09
Patent number
US04223032

Reaction notes

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