Preparation method and application of pyrazole oxime ether compound containing pyrimidine sulfide structure
A technology of pyrazole oxime ether and pyrimidine sulfide, which is applied in the field of pesticides to achieve excellent control effects
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Embodiment 1
[0028]
[0029] Dissolve 5 mmol of compound IIa in 30 mL of anhydrous DMF, then add 12 mmol of anhydrous potassium carbonate and 6 mmol of intermediate III, heat up to 55°C, and react for 10 hours. After the reaction solution was cooled to room temperature, it was poured into 100 mL of water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, separated and purified by column chromatography to obtain the target compound Ia. 1 H NMR (400MHz, CDCl 3 ): δ7.79(s, 1H, CH=N), 7.57(d, J=8.4Hz, 2H, Ar-H), 7.32(d, J=8.0Hz, 2H, Ar-H), 6.82(s ,4H,Ar-H),5.71(s,1H,Pyrimidine-H),5.03(s,2H,CH 2 ),3.77(s,3H,OCH 3 ),3.72(s,6H,2×OCH 3 ),3.60(s,3H,N-CH 3 ),2.35(s,3H,CH 3 ).
Embodiment 2
[0031]
[0032] 4 mmol of compound IIb was dissolved in 30 mL of acetonitrile, then 12 mmol of anhydrous potassium carbonate and 6 mmol of intermediate III were added, and the temperature was raised to reflux for 14 hours. After the reaction solution was cooled to room temperature, it was filtered with suction to remove the solid, the mother liquor was rotary evaporated to dryness under reduced pressure, and the obtained residue was separated and purified by column chromatography to obtain the target compound Ib. 1 H NMR (400MHz, CDCl 3 ): δ7.80(s, 1H, CH=N), 7.56(d, J=8.4Hz, 2H, Ar-H), 7.31(d, J=8.0Hz, 2H, Ar-H), 7.09(d ,J=8.0Hz,2H,Ar-H),6.77(d,J=8.8Hz,2H,Ar-H),5.70(s,1H,Pyrimidine-H),5.03(s,2H,CH 2 ),3.71(s,6H,2×OCH 3 ),3.58(s,3H,N-CH 3 ),2.35(s,3H,CH 3 ),2.30(s,3H,CH 3 ).
Embodiment 3
[0034]
[0035] 4 mmol of compound IIc was dissolved in 30 mL of acetonitrile, then 9 mmol of anhydrous potassium carbonate and 5 mmol of intermediate III were added, and the temperature was raised to reflux for 16 hours. After the reaction liquid was cooled to room temperature, it was suction-filtered to remove the solid, the mother liquor was rotary evaporated to dryness under reduced pressure, and the obtained residue was separated and purified by column chromatography to obtain the target compound Ic. 1 H NMR (400MHz, CDCl 3 ):δ7.81(s,1H,CH=N),7.56(d,J=8.0Hz,2H,Ar-H),7.29-7.33(m,4H,Ar-H),7.08-7.12(m, 1H, Ar-H), 6.88(d, J=8.0Hz, 2H, Ar-H), 5.70(s, 1H, Pyrimidine-H), 5.02(s, 2H, CH 2 ),3.72(s,6H,2×OCH 3 ),3.59(s,3H,N-CH 3 ),2.35(s,3H,CH 3 ).
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