反应详情

3,5-Diiodo-N′-(3-methoxybenzoyl)benzohydrazide (5.0 g, 9.58 mmol) was suspended in POCl3 (50.0 ml) and heating was started. During heating white solid of starting materials dissolved into a clear solution (130° C.). The reaction was kept at 100° C. and the reaction was monitor by thin layer chromatography. After 5 h, the reaction mixture was brought to room temperature and was carefully dropped into ice-water (1000.0 ml). White solid precipitated out was collected by filtration and washed with water. After dried, the crude product was purified by silica gel column chromatography eluting with dichloromethane and ethyl acetate in 9.5:0.5 ratio. After evaporating solvent the white solid was recrystallized from acetone/water and finally dried under vacuum. Pure product was obtained as white solid in 3.4 g (70.8%) yield. 1H NMR (400 MHz, CDCl3, δ): 8.43 (dd, J1=1.6 Hz, J2=0.8 Hz, 2H), 8.23 (t, J=1.6 Hz, 1H), 7.71 (d, J=8.0 Hz, 1H), 7.66 (m, 1H), 7.46 (t, J=8.0 Hz, 1H), 7.12 (dd, J1=8.0 Hz, J2=2.4 Hz, 1H), 3.92 (s, 3H, OCH3). 13C NMR (100 MHz, CDCl3, δ): 165.06, 161.67, 159.98, 148.05, 134.63, 130.31, 126.95, 124.44, 119.44, 118.56, 111.66, 94.98, 55.59.

1. temperatureheating
2. temperatureDuring heating white solid of starting materials
3. dissolutiondissolved into a clear solution (130° C.)
4. customwas kept at 100° C.
5. customwas brought to room temperature
6. customWhite solid precipitated out
7. filtrationwas collected by filtration
8. washwashed with water
9. customAfter dried
10. customthe crude product was purified by silica gel column chromatography
11. washeluting with dichloromethane and ethyl acetate in 9.5:0.5 ratio
12. customAfter evaporating solvent the white solid
13. customwas recrystallized from acetone/water
14. customfinally dried under vacuum
15. customPure product was obtained as white solid in 3.4 g (70.8%)
16. customyield