Schotten - Baumann Reaction

Schotten – Baumann reaction is used for commercial production of amides. It is the method of synthesis of amides by using acid chloride. It is named after German Chemists Carl Schotten and Eugen Baumann. As the reaction was first described by these two chemists in 1883. 

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                                       Carl Schotten                            Eugen Baumann 

Schotten – Baumann Reaction 

Schotten – Baumann reaction is a condensation reaction of organic chemistry.  In this reaction acid chloride (acyl halide) or anhydride reacts with amine (primary or secondary) and base to produce amide. General reaction is given below

Sometimes this reaction name also indicates the reaction between acid chloride (acyl halide) or anhydride with alcohol and base to produce ester. General reaction is given below

Examples of Schotten – Baumann Reaction 

Schotten – Baumann reaction also refers to benzoylation reaction of active hydrogen containing compounds. Some examples of schotten – baumann reaction are given below

  • Benzoylation of phenol

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  • Reaction of benzylamine with acetyl chloride   

  • Reaction of acid chloride with primary amine

  • Benzoylation of aniline - Reaction of acid chloride with primary amine (aromatic)

Mechanism of Schotten -Baumann Reaction 

The schotten – baumann reaction mechanism is given for reaction of amine with acid chloride and base. It can be exaplained by following two steps 

Step 1. Attack By Nitrogen Atom of Amine on Carbonyl Carbon of Acyl Halide

Nitrogen atom of secondary amine has a lone pair of electrons. So, it attacks on carbonyl carbon atom of acyl halide. Thus, the reaction begins. It leads to rearrangement of acyl halide and removal of halide. Thus, nitrogen gets attached with carbonyl carbon of acyl halide. Reaction is given below

Step 2. Deprotonation 

Now the compound formed in step 1 reacts with base. Hydrogen atom attached with nitrogen combines with hydroxyl ion of base and forms water molecule. Thus deprotonation takes place and nitrogen being more electronegative than hydrogen gets the electrons towards itself and forms amide. Reaction is given below

Applications of Schotten – Baumann Reaction 

This reaction is widely used in synthesis in organic chemistry. Few applications of this reaction are given below

  • It is used in synthesis of N-vanillyl nonanamide or capsaicin. 

  • It is used in synthesis of benzamide from benzoyl chloride and phenethylamine. 

  • It is used in acylation of benzylamine. 

  • It is used in Fischer synthesis of peptides. 

  • Products of this reaction such as ester and amides are very useful in many industries such as food, medicine etc. 

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