87604-96-4

Upstream product

• 87604-90-8 C₁₁H₁₂N₄O₂ 
• 25102-85-6 p-cyanobenzenediazonium chloride 
• 873-74-5 4-Aminobenzonitrile 

Downstream Products

• 87605-04-7 N-p-cyanophenyl-α-diazoacetamide 
• 104703-39-1 N-(4-Cyano-phenyl)-2-methoxy-acetamide 

Relevant academic research and scientific papers

Open chair nitrogen compounds. Part X. Thermolysis of α-diazoacetanilides in methanol: a convenient synthesis of α-methoxyacetanilides from ethyl N-(arylazo)glycinate

α-Diazoacetanilides (4), which are readily available from teh open-chair triazenes (2), undergo thermolysis in methanol solution to afford the α-methoxyacetanilides (5), an apparently rare type of ether/amide derivative.The methanolic thermolysis is inhib

Open-chain nitrogen compounds. Part IV. Synthesis of 5-hydroxy-1,2,3-triazoles from 1-aryl-3-(ethoxycarbonylmethyl)triazenes: a new route to α-diazo-N-arylacetamides

A series of triazenes of type ArN=N-NH-CH2CO2Et, N-arylazoglycine ethyl esters, have been prepared by coupling the arene diazonium salt, ArN2+*X-, with ethyl glycinate, NH2CH2CO2Et; an electron-withdrawing substituent, e.g.NO2, CN, CO2R, and Cl, in the ortho or para position of the aryl group is essential for efficient coupling.The p-substituted arylazoglycine ethyl esters cyclize when treated with alcoholic potassium hydroxide to afford the potassium salts of the 1-aryl-5-hydroxy-1,2,3-triazoles, which can be obtained free by acidification of the potassium salt solution with acetic acid.Reaction of the potassium salts with acetic anhydride yields the 1-aryl-5-acetoxy-1,2,3-triazoles.The 5-hydroxytriazoles, when heated in ethanol, rearrange to α-diazoacetanilides, ArNH*COCHN2.The diazoamides can be obtained in low yield directly from the triazenes by prolonged refluxing in ethanol. o-Substituted aryltriazenes do not cyclize under the same conditions but fragment to the arylamine.