引用本文:
王金玲, 刘登才, 尹业平. 高效低毒除草剂氟嘧磺隆的合成[J]. 应用化学,
2009, 26(4): 486-488.
Citation: WANG Jin-Ling, LIU Deng-Cai, YIN Ye-Ping. Synthesis of Primisulfuron[J]. Chinese Journal of Applied Chemistry, 2009, 26(4): 486-488.
Citation: WANG Jin-Ling, LIU Deng-Cai, YIN Ye-Ping. Synthesis of Primisulfuron[J]. Chinese Journal of Applied Chemistry, 2009, 26(4): 486-488.
高效低毒除草剂氟嘧磺隆的合成
摘要:
以硫脲和丙二酸二乙酯为起始原料,通过环化、甲基化、双氟甲氧基化、氧化、氨解、缩合6步单元反应,合成氟嘧磺隆(primisulfuron,Ⅵ)及中间体Ⅰ、Ⅱ、Ⅲ、Ⅳ、Ⅴ,反应总收率达30%。在甲醇钠作用下,硫脲和丙二酸二乙酯环化得到中间体Ⅰ,再经巯基与硫酸二甲酯反应得到中间体Ⅱ,再经羟基与二氟一氯甲烷反应得到中间体Ⅲ,再经S原子被H2O2氧化得中间体Ⅳ,其甲基砜基团被氨基取代得中间体Ⅴ,目标产物Ⅳ由中间体Ⅴ与邻甲氧羰基苯磺酰异氰酸酯反应得到。化合物Ⅰ、Ⅱ、Ⅲ、Ⅳ、Ⅴ、Ⅵ的结构通过1H NMR、MS进行确证,其纯度通过HPLC进行检测。
English
Synthesis of Primisulfuron
Abstract:
4,6-Bis(difluoromethoxy)-2-aminopyrimdine(Ⅵ) and its intermediates Ⅰ,Ⅱ,Ⅲ,Ⅳ,Ⅴ were synthesized by cyclization,methylation,difluoromethoxidation,oxidation and ammonolysis reactions in sequence with thiourea and diethyl malonate as materials.The total yield is 30%.In methanol sodium,compound Ⅰ was obtained by the cyclization of thiourea and diethyl malonate.Compound Ⅱ was obtained by the reaction of sulfenyl of compound Ⅰ with dimethyl sulfate,compound Ⅲ was obtained by the reaction of hydroxy of compound Ⅱ with chlorodifuoromethane,compound Ⅳ was obtained by the oxidation of sulfur of compound Ⅲ using hydrogen peroxide,compound Ⅴ was obtained by the substitution of methylsulfone group of compound Ⅳ with amino,compound Ⅵ was obtained from compound Ⅴ by reaction with o-methoxycarbo-nylbenzenylsulfylisocyanate.The structures of compounds Ⅰ,Ⅱ,Ⅲ,Ⅳ,Ⅴ,Ⅵ were characterized by 1H NMR,MS,and the purities were detected by HPLC.
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Key words:
- thiourea
- / diethyl malonate
- / primisulfuron
- / structure characterization
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