1,1'-Carbonyldiimidazole → HCID 67398462、化合物

3-(4-Methoxy-3-nitro-phenyl)-acrylic acid (compound of Example 6; 0.95 g, 4.25 mmol) was dissolved in DMF (15 mL) to which CDI (0.82 g, 5.10 mmol) was added and the reaction mixture was stirred at room temperature. After 45 min, N-hydroxy-butyramidine (0.52 g, 5.10 mmol) was added. The reaction mixture was stirred at room temperature for about 16-18 h. After completion of the reaction, additional CDI (0.82 g, 5.10 mmol) was added and the reaction mixture was refluxed at 110° C. to 120° C. for 6 h to effect cyclodehydration. DMF was evaporated and the reaction mixture was cooled to room temperature. Water (10 mL) was added to the reaction mixture followed by extraction with ethyl acetate (2×10 mL). The combined organic layers were washed with water (2×10 mL) and brine (10 mL). The organic phase obtained was dried over anhydrous sodium sulfate and concentrated to obtain a crude product, which was purified by column chromatography (silica gel, 0.25% ethyl acetate in petroleum ether) to afford the title compound.

1. additionwas added
2. stirringThe reaction mixture was stirred at room temperature for about 16-18 h
3. additionwas added
4. temperaturethe reaction mixture was refluxed at 110° C. to 120° C. for 6 h
5. customDMF was evaporated
6. temperaturethe reaction mixture was cooled to room temperature
7. additionWater (10 mL) was added to the reaction mixture
8. extractionfollowed by extraction with ethyl acetate (2×10 mL)
9. washThe combined organic layers were washed with water (2×10 mL) and brine (10 mL)
10. customThe organic phase obtained
11. dry with materialwas dried over anhydrous sodium sulfate
12. concentrationconcentrated
13. customto obtain a crude product, which
14. customwas purified by column chromatography (silica gel, 0.25% ethyl acetate in petroleum ether)

ORDレコード

ord-3d44d1524dcf49bb9f635e48501d5998

出典データセット

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08629277B2