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Acetamide (systematic name: ethanamide) is an organic compound with the formula CH 3 CONH 2. It is an amide derived from ammonia and acetic acid . It finds some use as a plasticizer and as an industrial solvent. [ 5 ]
While the conjugate acid of an amine has a pK a of about 9.5, the conjugate acid of an amide has a pK a around −0.5. Therefore, compared to amines, amides do not have acid–base properties that are as noticeable in water. This relative lack of basicity is explained by the withdrawing of electrons from the amine by the carbonyl.
Dry acetamidine hydrochloride releases acetonitrile, while in aqueous solution, it instead undergoes hydrolysis to acetic acid and ammonia. [3] CH 3 C(NH)NH 2 ·HCl → CH 3 CN + NH 4 Cl CH 3 C(NH)NH 2 ·HCl + 2 H 2 O → CH 3 COOH + NH 3 + NH 4 Cl. As free base amidines are strong Lewis bases, acetamidine hydrochloride is a weak Lewis acid ...
DMA is prepared commercially by the reaction of dimethylamine with acetic anhydride or acetic acid. Dehydration of the salt of dimethylamine and acetic acid also furnishes this compound: [5] CH 3 CO 2 H·HN(CH 3) 2 → H 2 O + CH 3 CON(CH 3) 2. Dimethylacetamide can also be produced by the reaction of dimethylamine with methyl acetate. [6]
A notable method for synthesizing acetamidomalon ester is described in a 1950 patent, [1] which cites a procedure previously featured in Organic Syntheses. [2] The synthesis procedure involves the preparation of malonic acid diethyl ester in acetic acid combined with sodium nitrite (NaNO 2), resulting in diethyl isonitrosomalonate (also known as α-oximinomalonic acid diethyl ester).
Hydrazine is used to convert the ester to an acylhydrazine, which is reacted with nitrous acid to give the acyl azide. Heating the azide in ethanol yields the ethyl carbamate via the Curtius rearrangement. Acid hydrolysis yields the amine from the carbamate and the carboxylic acid from the nitrile simultaneously, giving the product amino acid. [20]
The name "Schotten–Baumann reaction conditions" often indicate the use of a two-phase solvent system, consisting of water and an organic solvent. The base within the water phase neutralizes the acid, generated in the reaction, while the starting materials and product remain in the organic phase, often dichloromethane or diethyl ether.
The Leuckart reaction is the chemical reaction that converts aldehydes or ketones to amines.The reaction is an example of reductive amination. [1] The reaction, named after Rudolf Leuckart, uses either ammonium formate or formamide as the nitrogen donor and reducing agent.