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Concept
Acetamide
Summary
Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. It is derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent. The related compound N,N-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide. Acetamide can be considered an intermediate between acetone, which has two methyl (CH3) groups either side of the carbonyl (CO), and urea which has two amide (NH2) groups in those locations. Acetamide is also a naturally occurring mineral with the IMA symbol: Ace.
Acetamide can be produced in the laboratory from ammonium acetate by dehydration:
[NH4][CH3CO2] → CH3C(O)NH2 + H2O
Alternatively acetamide can be obtained in excellent yield via ammonolysis of acetylacetone under conditions commonly used in reductive amination.
It can also be made from anhydrous acetic acid, acetonitrile and very well dried hydrogen chloride gas, using an ice bath, alongside more valuable reagent acetyl chloride. Yield is typically low (up to 35%), and the acetamide made this way is generated as a salt with HCl.
In a similar fashion to some laboratory methods, acetamide is produced by dehydrating ammonium acetate or via the hydration of acetonitrile, a byproduct of the production of acrylonitrile.:
CH3CN + H2O → CH3C(O)NH2
Acetamide is used as a plasticizer and an industrial solvent. Molten acetamide is good solvent with a broad range of applicability. Notably, its dielectric constant is higher than most organic solvents, allowing it to dissolve inorganic compounds with solubilities closely analogous to that of water. Acetamide has uses in electrochemistry and the organic synthesis of pharmaceuticals, pesticides, and antioxidants for plastics. It is a precursor to thioacetamide.
Acetamide has been detected near the center of the Milky Way galaxy. This finding is potentially significant because acetamide has an amide bond, similar to the essential bond between amino acids in proteins.
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