C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 495/04 (2006.01)
Patent
CA 2193774
A process for producing 1-hydroxythienoimidazole carboxylic acid represented by formula (2): (see formula 2) wherein R1 and R2 are as defined in the specification; wherein the process comprises the steps of: (a) reacting thienoimidazole represented by formula (1) with 1,4-dihalogenodimagnesium butane, in the presence of tetrahydrofuran or a mixed solvent comprising tetrahydrofuran and an aromatic solvent to produce a reaction mixture: (see formula 1) wherein R1 and R2 are as defined above; (b) adding the reaction mixture obtained in the step (a) and, optionally, carbon dioxide, to: (i) a solution comprising carbon dioxide and tetrahydrofuran, or (ii) a solution comprising carbon dioxide, tetrahydrofuran and an aromatic solvent to give a reaction liquid; and (c) hydrolyzing the reaction liquid. Alternatively, a process for producing 1-hydroxythienoimidazole carboxylic acid represented by formula (2), wherein the process comprises the steps of: (a) reacting a thienoimidazole represented by formula (1) with 1,4-dihalogenodimagnesium butane, in the presence of tetrahydrofuran or a mixed solvent comprising tetrahydrofuran and an aromatic solvent to produce a reaction mixture, and wherein the thienoimidazole represented by formula (1) is added to the 1,4-dihalogenodimagnesium butane either solely or in cake state or slurry state, wherein the cake state and slurry state are made by adding a small amount of either tetrahydrofuran or a mixed solvent comprising tetrahydrofuran and an aromatic solvent; (b) reacting the reaction mixture obtained in step (a) with carbon dioxide to produce a reaction liquid; and (c) hydrolyzing the reaction liquid. Additionally, a process of producing thienoimidazole carboxylic acid represented by formula (3): (see formula 3) wherein R1 and R2 are as defined above utilizing the above processes.
Hirata Norihiko
Miyamoto Yasunobu
Mizuno Masahiko
Takahashi Toshiya
Fetherstonhaugh & Co.
Sumitomo Chemical Company Limited
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