申请人:ISHIHARA SANGYO KAISHA LTD.
公开号:EP0705823A1
公开(公告)日:1996-04-10
A process for producing 1-substituted-2-cyanoimidazole compounds is described, which comprises (1) undergoing a reaction of a compound represented by formula (IV), hydroxylamine or a mineral acid salt thereof, and glyoxal or glyoxime to produce a compound represented by formula (III), (2) undergoing a reaction of the compound represented by formula (III) with thionyl chloride or thionyl bromide in the presence of N,N-dialkylamide to produce a reaction mixture, and then reacting the produced reaction mixture with sulfur chloride to produce a 2-cyanoimidazole compound represented by formula (II), and (3) undergoing a sulfamoylation reaction and an isomerization reaction of the 2-cyanoimidazole compound represented by formula (II) and a compound represented by formula (V) in the presence of at least one base selected from carbonates of alkali metals and bicarbonates of alkali metals and a polar solvent to produce a 1-substituted-2-cyanoimidazole compound represented by formula (I-b). The substituents in formulae are specifically defined in the specification.
Hal-SO₂N(R¹)R (V)
本发明描述了一种生产 1-取代-2-氰基咪唑化合物的工艺,该工艺包括:(1) 将式(IV)代表的化合物、羟胺或其矿物酸盐与乙二醛或乙二醛肟反应,生成式(III)代表的化合物;(2) 在 N,N-二烷基酰胺存在下,将式(III)代表的化合物与亚硫酰氯或亚硫酰溴反应,生成反应混合物、然后将生成的反应混合物与氯化硫反应,生成由式(II)代表的 2-氰基咪唑化合物、和 (3) 在至少一种选自碱金属碳酸盐和碱金属碳酸氢盐的碱和极性溶剂存在下,使式 (II) 所代表的 2-氰基咪唑化合物和式 (V) 所代表的化合物发生氨基磺酰化反应和异构化反应,生成式 (I-b) 所代表的 1-取代基-2-氰基咪唑化合物。式中的取代基在说明书中有具体定义。
Hal-SO₂N(R¹)R (V)