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
| 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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