反应详情

温度

90 °C

4-(3-Dimethylamino-2-methoxymethyl-acryloyl)-1H-pyrrole-2-carboxylic acid (2-hydroxy-1-(S)-phenyl-ethyl)-amide (17.6 mmol, 6.0 g) was combined with thiourea (39 mmol, 3.0 g) and potassium carbonate (53 mmol, 7.3 g) in ethanol (50 mL) and the resulting suspension was heated at 90° C. for 24 hrs. The solvent was removed in vacuo and the resulting black solid was diluted with water and the solid was removed by filtration. The solid was washed with ethyl acetate twice and the aqueous solution was acidified to pH 5-6 with HCl (2N). The solid formed was removed by filtration and the aqueous solution was then extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate. The solvent was removed under vacuum to afford the title compound as a brown solid (3.0 g, 48% yield). HPLC Method B, Rt=3.7 minutes, 1H NMR consistent with structure.

1. customThe solvent was removed in vacuo
2. additionthe resulting black solid was diluted with water
3. customthe solid was removed by filtration
4. washThe solid was washed with ethyl acetate twice
5. customThe solid formed
6. customwas removed by filtration
7. extractionthe aqueous solution was then extracted twice with ethyl acetate
8. dry with materialThe combined organic phases were dried over sodium sulfate
9. customThe solvent was removed under vacuum