117713-58-3

Basic information

• Product Name: N-methylbenzamide
• Synonyms: N-methylbenzamide
• CAS NO: 117713-58-3
• Molecular Weight: 137.166
• Mol File: 117713-58-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-methylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-methylbenzamide(117713-58-3)
• EPA Substance Registry System: N-methylbenzamide(117713-58-3)

Safety Data

• Hazardous Substances Data: 117713-58-3(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 100-47-0 benzonitrile 
• 109-99-9 tetrahydrofuran 
• 14906-64-0 3-cyanopyridine N-oxide 
• 1004-10-0 [¹⁸O]-benzoyl chloride 
• 74-89-5 methylamine 
• 21737-87-1 N-methyl benzimidoyl chloride 

Relevant articles and documents

Regioselective Three-Component Reaction of Pyridine N-Oxides, Acyl Chlorides, and Cyclic Ethers

A novel three-component reaction of pyridine N-oxides, acyl chlorides, and cyclic ethers is described. Treatment of an electron-deficient pyridine N-oxide with an acyl chloride in the presence of a cyclic ether at 25-50 °C leads to a substituted pyridine as a single regioisomer in up to 58% isolated yield. Isotopic-labeling experiments and substrate scope support the reaction proceeding through a carbene intermediate.

Kinetics and Mechanism of the Hydrolysis of N-Methyl-N-nitroamides in Aqueous Sulphuric Acid

Pseudo first-order rate constants for the hydrolysis of N-methyl-N-nitroacetamide and various 4-substituted N-methyl-N-nitrobenzamides in sulphuric acid solutions are reported.N-Methyl-N-nitroacetamide undergoes an acid-catalysed process at all acidities studied for which the solvent deuterium isotope effect, k0H2SO4/k0D2SO4, is 0.87, and ΔS(excit.) ca. -85 (+/-10) J K-1 mol-1.These results suggest an AAc2 mechanism involving rapid pre-equilibrium protonation of the substrate followed by rate-limiting attack of water at the carbonyl C-atom to form atetrahedral intermediate which collapses, in a fast step, to the products.The N-methyl-N-nitrobenzamides, however, exhibit both non-catalysed and acid-catalysed hydrolysis.The non-catalysed pathway operates at acidities up to ca. 5 mol dm-3 H2SO4, and is characterised by a solvent deuterium isotope effect, k0H2SO4/k0D2SO4, of 1.5, ΔS(excit.) ca. -100 (+/-10) J K-1 mol-1 and a Hammett ρ value of 1.0 (+/-0.1).No catalysis by Br- is observed and the results are more consistent with a thermal rearrangement and expulsion of N2O.The acid-catalysed pathway operates at acidities >5 mol dm-3 H2SO4.The solvent deuterium isotope effect k0H2SO4/k0D2SO4 is 0.58, ΔS(excit.)>0 JK-1 mol-1 and the Hammett ρ value is -3.4 (+/-0.1).Thus a change in mechanism occurs at ca. 5 mol dm-3 H2SO4 to an Ac1 pathway involving protonation of the substrate, followed by rate-limiting cleavage of the amide C-N bond to form a benzoyl cation.The different acid-catalysed hydrolysis pathways for the N-nitroacetamide and N-nitrobenzamides is ascribed to the stabilisation afforded to the benzoyl cation as opposed to the carbonium ion.N-Nitroamides are hydrolysed exclusively via amide C-N bond cleavage whereas the correspondning N-nitrosoamides decompose via concurrent C-N and N-N (i.e. denitrosation) bond cleavage.This difference between N-nitro and N-nitroso-amides is discussed in terms of the greater stability of the NO+ group.