Schotten–Baumann reaction

The Schotten–Baumann reaction is a method to synthesize amides from amines and acid chlorides: Schotten–Baumann reaction also refers to the conversion of acid chloride to esters.

The reaction was first described in 1883 by German chemists Carl Schotten and Eugen Baumann.

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.

[3][4][5] Examples: In the Fischer peptide synthesis (Emil Fischer, 1903),[6] an α-chloro acid chloride is condensed with the ester of an amino acid.

In a final step the chloride atom is replaced by an amino group, completing the peptide synthesis.

An example of a Schotten-Baumann reaction. Benzylamine reacts with acetyl chloride under Schotten-Baumann conditions to form N -benzylacetamide.