Citation:
WANG Jin-Ling, LIU Deng-Cai, YIN Ye-Ping. Synthesis of Primisulfuron[J]. Chinese Journal of Applied Chemistry,
;2009, 26(4): 486-488.
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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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Keywords:
- thiourea,
- diethyl malonate,
- primisulfuron,
- structure characterization
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