反应详情

A mixture of 3-aminorhodanine (148 mg, 1.00 mmol), 1-(3,4-dimethylphenyl)-5-hydroxy-3-methyl-1H-pyrazole-4-carbaldehyde (230 mg, 1.00 mmol) and ethanol (10 mL) was stirred 96 h. The solid was filtered, washed with ethanol and ether and dried. A mixture of the resulting crude imine (80 mg, 0.222 mmol), piperidine (2 mg, 0.022 mmol), 4-formylbenzoic acid (33 mg, 0.222 mmol), benzoic acid (3 mg, 0.022 mmol) and toluene (10 mL) was heated under reflux for 6 h in an apparatus fitted with a Dean and Stark separator to remove water. After cooling, the solid was filtered off, washed with toluene and ether, and purified by reverse phase HPLC (CombiPrep ODS-A, 10-90% acetonitrile/water+0.1% trifluoroacetic acid) to give the title compound (18 mg, 16%) as a solid. LCMS, m/e 493 [M+H]+.

1. filtrationThe solid was filtered
2. washwashed with ethanol and ether
3. customdried
4. temperaturewas heated
5. temperatureunder reflux for 6 h in an apparatus
6. customfitted with a Dean and Stark separator
7. customto remove water
8. temperatureAfter cooling
9. filtrationthe solid was filtered off
10. washwashed with toluene and ether
11. custompurified by reverse phase HPLC (CombiPrep ODS-A, 10-90% acetonitrile/water+0.1% trifluoroacetic acid)