26487-08-1

Usage

InChI:InChI=1/C10H10N2O/c1-12(2)10(13)9-6-4-3-5-8(9)7-11/h3-6H,1-2H3

Upstream product

• 7468-67-9 o-formylbenzonitrile 
• 68-12-2 N,N-dimethyl-formamide 
• 3839-22-3 2-cyanobenzoic acid 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 611-74-5 N,N-dimethylbenzamide 
• 214360-47-1 2-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-benzonitrile 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 27611-63-8 2-Cyanobenzoyl chloride 
• 124-40-3 dimethyl amine 
• 6587-24-2 methyl 2-cyanobenzoate 

Relevant academic research and scientific papers

Copper-catalyzed amide bond formation from formamides and carboxylic acids

A highly efficient copper-catalyzed approach to form amide bonds from formamides and carboxylic acids was developed. This protocol shows broad substrate scopes and high yields in the presence of 1 mol% catalyst and 4.0 equiv. formamides.

Versatile ruthenium(ii)-catalyzed C-H cyanations of benzamides

Direct cyanations of arenes and heteroarenes bearing only weakly coordinating amides were accomplished using a robust ruthenium(ii) catalyst. The user-friendly C(sp2)-H activation occurred with the assistance of carboxylate with high site-selectivity, excellent functional group tolerance and ample scope.

Cross coupling of acyl and aminyl radicals: Direct synthesis of amides catalyzed by Bu4NI with TBHP as an oxidant

A radical solution: A Bu4NI/tert-butyl hydroperoxide (TBHP) catalyzed synthesis of amides through a cross-coupling reaction between acyl and aminyl radicals is described. This method involves the combination of aldehyde C-H bond functionalization and decarbonylation of N,N-disubstituted formamides (see scheme). The cross-coupling is metal-free, has a wide substrate scope, operational simplicity, and gives high yields on scale-up. Copyright

Synthesis of tertiary benzamides via Pd-catalyzed coupling of arylboronic esters and carbamoyl chlorides

Ortho-substituted arylboronic esters are efficiently coupled with carbamoyl chlorides under Pd-catalysis to give tertiary benzamides.

INVESTIGATIONS ON N,N-DIALKYLBENZAMIDES BY NMR SPECTROSCOPY. PART IV. COMPARISON OF BARRIERS TO ROTATION ABOUT THE AMINE C-N BOND IN ORTHO-SUBSTITUTED N,N-DIMETHYL-AND N,N-DIETHYLBENZAMIDES

The barriers to rotation about the amide C-N bond in a series of ortho-substituted N,N-dimethyl and N,N-diethylbenzamides have been compared.It has been stated that for most of substituents, namely CH3, Cl, Br, I and NO2, the rates of rotation in both series of compounds are identical within the accuracy of measurement (kEt/kMe ca.1).The remaining compounds (F, CN, CH3) show a higher rate of rotation in the series of diethylbenzamides (kEt/kMe ca.1,5).An exception are the OH derivatives in which the internal H-bond is present and because of that the barrier to rotation is lowered and the kEt/kMe ratio raised up to 2.3.