反应详情

温度

108 °C

4,5-Diamino-2-trifluoromethyl-benzonitrile (4.14 g; 20.6 mmoles) and 3,3,3-trifluoro-2-hydroxy-propionic acid (4.50 g; 31.2 mmoles) were suspended in 6N HCl (7 mL; 42 mmoles) under a nitrogen atmosphere. The reaction was stirred vigorously and heated to 108° C. for 18 hrs, then cooled to room temperature. The reaction was diluted with water (100 mL) and with ethyl acetate (100 mL), then sodium bicarbonate (5.19 g; 62.0 mmoles) was added slowly and in portions to quench the reaction. The aqueous layer was separated and extracted with ethyl acetate (3×40 mL). The extracts were combined, washed with water (30 mL) and brine (30 mL), then dried over Na2SO4. The filtrate was concentrated in vacuo to yield a crude dark solid which was then purified by column chromatography (SiO2; 30% ethyl acetate/CH2Cl2) to yield the title compound as a dark brown solid.

1. temperaturecooled to room temperature
2. customto quench
3. customthe reaction
4. customThe aqueous layer was separated
5. extractionextracted with ethyl acetate (3×40 mL)
6. washwashed with water (30 mL) and brine (30 mL)
7. dry with materialdried over Na2SO4
8. concentrationThe filtrate was concentrated in vacuo
9. customto yield a crude dark solid which
10. customwas then purified by column chromatography (SiO2; 30% ethyl acetate/CH2Cl2)