反应详情

温度

100 °C

4-Fluoro-N,N-dimethyl-3-nitrobenzamide 1.21 g, 2-m-tolyl-1H-imidazole 600 mg, potassium carbonate 524 mg and N,N-dimethylacetamide 20 mL were mixed and stirred in nitrogen atmosphere for 12 hours at 100° C. After cooling off, the reaction liquid was diluted with ethyl acetate, and water was added to effect phase separation. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and from which the solvent was distilled off. Thus obtained crude product was dissolved in acetic acid 10 mL and water 10 mL, and to the solution 85% sodium hyposulfite 2.65 g was added, followed by 2 hours' heating under reflux. The reaction liquid was cooled with ice and neutralized with saturated sodium hydrogencarbonate solution, which was then extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. Distilling the solvent off, the resulting compound was mixed with 1,1′-carbonyldiimidazole 924 mg and 1,2-dichlorobenzene 30 mL, followed by heating under reflux for 10 hours in nitrogen, atmosphere. The reaction liquid was filtered to remove the insoluble matter, and then the solvent was distilled off. Purifying the product on silica gel column chromatography (chloroform:methanol=10:1) and P-TLC (chloroform:methanol=20:1) by the order stated, 112 mg of the title compound was obtained.

1. temperatureAfter cooling off
2. customthe reaction liquid
3. additionwas added to effect phase separation
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. distillationfrom which the solvent was distilled off
7. customThus obtained crude product
8. waitfollowed by 2 hours
9. temperature' heating
10. temperatureunder reflux
11. customThe reaction liquid
12. extractionwas then extracted with ethyl acetate
13. washThe extract was washed with saturated brine
14. dry with materialdried over anhydrous sodium sulfate
15. distillationDistilling the solvent off, the resulting compound
16. additionwas mixed with 1,1′-carbonyldiimidazole 924 mg and 1,2-dichlorobenzene 30 mL
17. temperatureby heating
18. temperatureunder reflux for 10 hours in nitrogen
19. customThe reaction liquid
20. filtrationwas filtered
21. customto remove the insoluble matter
22. distillationthe solvent was distilled off
23. customPurifying the product on silica gel column chromatography (chloroform:methanol=10:1) and P-TLC (chloroform:methanol=20:1) by the order