Esterification/Amidation

Triazine-type

Triazine condensing agents such as DMT-MM are one of attractive condensing agents. The advantage of this reagent is that low alcohol or water can be used as a solvent for esterification or amidation reaction. It is a very useful for the reaction of water or lower alcohol soluble material. Since by-product that is generated from DMT-MM after reaction is water-soluble, they can be easily removed by washing at extraction step.

Application

The amidation reaction in alcohol solvents

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Run Condensing agent Solvent Amide(3)a Estera(%) Amide/Ester
1 DMT-MM MeOH 98 1.0(R=Me) 98
2 DMT-MM EtOH 99 0.7(R=Et) 141
3 DMT-MM i-PrOH 96 0.7(R=i-Pr) 137
4 DCC MeOH 27b 7.0(R=Me) 4
5 EDC MeOH 53 16.0(R=Me) 3.3

*a:Isolated yield
*b:N-Acylurea was isolated in 21%

References
  • Kunishima, M., Kawachi, C., Morita, J., Terao, K., Iwasaki, F. and Tani, S. : Tetrahedron, 55, 13159 (1999).
  • M. Kunishima, C. Kawachi, K. Hioki, K. Terao, S. Tani : Tetrahedron, 57, 1551(2001).

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