Ethyl cyanoacetate → ethyl 5-amino-1-p-tolyl-1H-1,2,3-triazole-4-carboxylate

HRID 27689Notes

Reaction equation

HRID 27689 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([N:7]=[N+:8]=[N-:9])=[CH:3][CH:2]=1.[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12]>CCO>[NH2:12][C:11]1[N:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=2)[N:8]=[N:9][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 1374301-Azido-4-methylbenzene

Product 1

HCID 12699267ethyl 5-amino-1-p-tolyl-1H-1,2,3-triazole-4-carboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reaction of p-tolyl azide (9.38 g; 0.0705 mole) with ethyl cyanoacetate (7.96 g: 0.0705 mole) as described in example 1a gave 12.76 g (74%) of the triazole of mp (EtOH) 152-153° C. (lit mp 147.5° C., B. R. Brown, D. L. Hammick and S. G. Heritage J. Chem. Soc. 3870 [1953]). (Found; C, 58.38; H 5.90; N, 22.89; C12H14N4O2 requires; C, 58.52; H, 5.73; N, 22.75%).

Sources & evidence

ORD record
ord-c46b9c2f3e4f410c85dd4d7b9191d154
Source dataset
uspto-grants-1980_09
Patent number
US04223032

Reaction notes

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