Schotten Baumann Reaction

Introduction

Schotten Baumann reaction refers to the method of chemically synthesizing amides from acyl chlorides and amines. This organic chemical reaction is named after the German chemists Carl Schotten and Eugen Baumann, who discovered this method of synthesizing amides.

Table of Contents

• • Features of Schotten Baumann Reaction
  • Schotten Baumann Reaction Mechanism
  • Applications of Schotten Baumann Reaction

Features of Schotten Baumann Reaction

The Schotten Baumann reaction can also refer to the benzoylation of active hydrogen-containing compounds with the help of benzyl chloride and aqueous sodium hydroxide. Pyridine can also be used as an alternative to the sodium hydroxide base.

This reaction can be generalized as follows.

Schotten Baumann Reaction

Some key features of the Schotten Baumann Reaction are:

• It is a base-catalyzed reaction. The base is necessary to encourage an equilibrium shift towards the formation of amides.
• The base also neutralizes the hydrochloric acid which is formed in the process, thereby preventing the further protonation of the amide product formed.
• Usually, aqueous sodium hydroxide is used as the base catalyst, but pyridine also can be used in this reaction.
• It is generally observed that the acyl chlorides are converted into acylating agents of superior power when pyridine is used as the base catalyst.

The ‘Schotten Baumann conditions’ maintained in this reaction refer to the aqueous basic environment which is biphasic in nature.

Schotten Baumann Reaction Mechanism

The mechanism of this reaction can be broken down into three steps in order to easily understand it. These steps are:

Step 1

The formation of a protonated compound from the reaction between the acyl chloride and the amine. First, the nitrogen atom puts forth a lone pair of electrons towards the formation of a carbon-nitrogen bond

The positive and negative charges on the nitrogen and oxygen atoms are neutralized by the exchange of a proton between them.

Step 2

The catalyst of the reaction (i.e. the base) proceeds to absorb the acidic proton which is formed when oxygen attempts to reform a double bond with the carbonyl carbon (which is favourable as the electronegative chlorine atom can easily break its bond with carbon and be liberated as a chloride ion).

Step 3

In the final step of the Schotten Baumann reaction mechanism, the required amide product is formed along with hydrochloric acid now that the base catalyst has absorbed the acidic proton. This HCl is neutralized by the base catalyst as well.

Mechanism of Schotten Baumann Reaction

The entire mechanism of the Schotten Baumann Reaction is illustrated above.

Applications of Schotten Baumann Reaction

Some important applications of this reaction are listed below.

• • • • The reaction and its conditions are used in the synthesis of synthetic capsaicin and phenethylamine.
      • The acylation of benzylamines can be done using this process with the help of either acetyl chloride or acetic anhydride.
      • Some concepts used in the Schotten Baumann reaction are also used in the Fischer synthesis of peptides.

Thus, it can be noted that the Schotten Baumann reaction is a very important named reaction in organic chemistry, having numerous applications.