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Transamidation
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Transamidation is a chemical reaction in which an reacts with an to generate a new amide:
RC(O)NR'2 + HNR"2 → RC(O)NR"2 + HNR'2

The reaction is rarely employed, but it could prove relevant to peptide synthesis.

Amides are characteristically inert, but the amino substituents can be exchanged in the presence of and . Primary amides (RC(O)NH2) are more amenable to this reaction.


Ureas
In contrast to the reluctance of amides as substrates, is more susceptible to this exchange process. Transamidation is practiced, sometimes even on an industrial scale, to prepare a variety of N-substituted :
(H2N)2CO + R2NH → (R2N)(H2N)CO + NH3
(R2N)(H2N)CO + R2NH → (R2N)2CO + NH3
Methylurea, precursor to , is produced from and urea. Phenylurea is produced similarly but from anilinium chloride:
(H2N)2CO + C6H5NH3Cl → (C6H5(H)N)(H2N)CO + NH4Cl

derivatives of urea are often produced by transamidation-like reactions. These products include , , and .


Further reading

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