Amide
Reaction name Substrate Details
Nucleophilic acyl substitution acyl chloride or acid anhydride Reagent : ammonia or amines
Beckmann rearrangement Cyclic ketone Reagent : hydroxylamine and acid
Schmidt reaction Ketones Reagent : hydrazoic acid
Nitrile hydrolysis Nitrile Reagent : water ; acid catalyst
Willgerodt-Kindler reaction Aryl alkyl ketones Sulfur and morpholine
Passerini reaction Carboxylic acid , ketone or aldehyde
Ugi reaction Isocyanide , carboxylic acid , ketone , primary amine
Bodroux reaction Carboxylic acid , Grignard reagent with an aniline derivative ArNHR′
Chapman rearrangement Aryl imino ether For N , N -diaryl amides . The reaction mechanism is based on a nucleophilic aromatic substitution
Leuckart amide synthesis Isocyanate Reaction of arene with isocyanate catalysed by aluminium trichloride , formation of aromatic amide
Ritter reaction Alkenes , alcohols , or other carbonium ion sources Secondary amides via an addition reaction between a nitrile and a carbonium ion in the presence of concentrated acids
Photolytic addition of formamide to olefins Terminal alkenes A free radical homologation reaction between a terminal alkene and formamide
Ester aminolysis Esters Base catalyzed reaction of esters with various amines to form alcohols and amides
Synthesis
Many methods exist in amide synthesis . [ 11 ] On paper , the simplest method for making amides is by coupling a carboxylic acid with an amine . In general this reaction is thermodynamically favorable , however it suffers from a high activation energy , largely due to the amine first deprotonating the carboxylic acid , which reduces its reactivity . As such the direct reaction often requires high temperatures . RCO2H + R′R″NH ⇌ RCO−2 + R′R″NH+2 ⇌ RC ( O ) NR′R″ + H2O Many methods are known for driving the equilibrium to the right . For the most part these reactions involve `` activating '' the carboxylic acid by first converting it to a better electrophile ; such as esters , acid chlorides ( Schotten-Baumann reaction ) or anhydrides ( Lumière–Barbier method ) . Conventional methods in peptide synthesis use coupling agents such as HATU , HOBt , or PyBOP . [ 12 ] In recent years there has also been a surge in the development of Boron reagents for amide bond formation , including catalytic use of 2-IodoPhenylBoronic acid [ 13 ] or MIBA , [ 14 ] and Tris ( 2,2,2-trifluoroethyl ) borate . [ 15 ] [ 16 ]
An amide ( or or ), also known as an acid amide, is a compound with the functional group RE(O)NR′ (R and R′ refer to H or organic groups). Most common are carboxamides (organic amides) (n = 1, E = C, x = 1), but many other important types of amides are known, including phosphoramides (n = 2, E = P, x = 1 and many related formulas) and sulfonamides (E = S, x = 2). The term amide refers both to classes of compounds and to the functional group (RE(O)NR′) within those compounds. Amide can also refer to azanide (the anion HN, conjugate base of ammonia) or to an organic amine (an anion RN). For discussion of these anionic amides, see Alkali metal amides. Due to the dual use of the word 'amide', there is debate as to how to properly and unambiguously name the derived anions of amides in the first sense (i.e., deprotonated acylated amines), a few of which are commonly used as nonreactive counterions. The remainder of this article is about the carbonyl-nitrogen sense of amide.