Chemistry:Schotten–Baumann reaction

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Short description: Method to synthesize amides from amines and acid chlorides
Schotten-Baumann reaction
Named after Carl Schotten
Eugen Baumann
Reaction type Condensation reaction
Identifiers
Organic Chemistry Portal schotten-baumann-reaction
RSC ontology ID RXNO:0000165

The Schotten–Baumann reaction is a method to synthesize amides from amines and acid chlorides:

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

Schotten–Baumann reaction also refers to the conversion of acid chloride to esters. The reaction was first described in 1883 by Germany chemists Carl Schotten and Eugen Baumann.[1][2]

The name "Schotten–Baumann reaction conditions" often indicate the use of a two-phase solvent system, consisting of water and an organic solvent. 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.

Applications

The Schotten–Baumann reaction or reaction conditions are widely used in organic chemistry.[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. The ester is then hydrolyzed and the acid converted to the acid chloride enabling the extension of the peptide chain by another unit. In a final step the chloride atom is replaced by an amino group completing the peptide synthesis.

Further reading

See also

References

  1. W Pötsch. Lexikon bedeutender Chemiker (VEB Bibliographisches Institut Leipzig, 1989) (ISBN:3-323-00185-0)
  2. M B Smith, J March. March's Advanced Organic Chemistry (Wiley, 2001) (ISBN:0-471-58589-0)
  3. Kent, R. E.; McElvain, S. M. (1945). "Isobutyramide". Organic Syntheses 25: 58. doi:10.15227/orgsyn.025.0058. 
  4. Cope, Arthur C.; Ciganek, Engelbert (1959). "N,N-Dimethylcyclohexylmethylamine". Organic Syntheses 39: 19. doi:10.15227/orgsyn.039.0019. 
  5. X. Wang; S. O. de Silva; J. N. Reed; R. Billadeau; E. J. Griffen; A. Chan; V. Snieckus (1995). "7-Methoxyphthalide". Organic Syntheses 72: 163. doi:10.15227/orgsyn.072.0163. 
  6. Emil Fischer (1903). "Synthese von Polypeptiden". Berichte der deutschen chemischen Gesellschaft 36 (3): 2982–2992. doi:10.1002/cber.19030360356. https://zenodo.org/record/1426082.