Table 1.
Condensation reaction of I and II in the presence of CDET/NMM in different solvents.
| Entry | Solvent | Coupling Agent (a) | Yield (%) (b) (15 min/60 min) |
|---|---|---|---|
| 1 | methanol | CDET/NMM | 88/91 |
| 2 | ethanol | CDET/NMM | 86/89 |
| 3 | propan-2-ol | CDET/NMM | 79/86 |
| 4 | H2O | CDET/NMM | 42/50 (c) |
| 5 | H2O/Acetone (90/10) | CDET/NMM | 88/90 |
Reaction conditions: benzoic acid (I): 1.3 mmol, phenylethylamine (II): 1.2 mmol, Solvent: 6 mL, T: 25 °C. (a) Coupling agent: 1.3 mmol of 2-chloro-4,6-diethoxy-1,3,5-triazine and 1.3 mmol of NMM were added. (b) Yield in III was measured by GLC using mesitylene as internal standard (1.2 mmol). (c) Yields were measured on the weight of III recovered after workup.