Process for producing 1-hydroxythienoimidazole carboxylic acid and thienoimidazole carboxylic acid

A process for producing 1-hydroxythieno carboxylic acid represented by formula (2):

• ##STR10## wherein R.sup.1 and R.sup.2 are each selected from the group consisting of an aralkyl group and allyl group, wherein said aralkyl group and allyl group are unsubstituted or substituted by one member selected from the group consisting of an alkyl group, alkoxyl group, nitro group, and halogen atom;
• wherein said 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:
• ##STR11## wherein R.sup.1 and R.sup.2 are as defined above;
• and wherein said thienoimidazole represented by formula (1) is added to said 1,4-dihalogenodimagnesium butane either directly or in a cake state or slurry state, wherein said 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 said reaction mixture obtained in step (a) with carbon dioxide to produce a reaction liquid;
• and
• (c) hydrolyzing said reaction liquid.

A process for producing thienoimidazole carboxylic acid represented by formula (3):

• ##STR12## wherein R.sup.1 and R.sup.2 are each selected from the group consisting of an aralkyl group and allyl group, wherein said aralkyl group and allyl group are unsubstituted or substituted by one member selected from the group consisting of an alkyl group, alkoxyl group, nitro group, and halogen atom;
• wherein said 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:
• ##STR13## wherein R.sup.1 and R.sup.2 are as defined above;
• (b) adding the reaction mixture obtained in said 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 and dehydrating said reaction liquid.

A process for producing thienoimidazole carboxylic acid represented by formula (3):

• ##STR14## wherein R.sup.1 and R.sup.2 are each selected from the group consisting of an aralkyl group and allyl group, wherein said aralkyl group and allyl group are unsubstituted or substituted by one member selected from the group consisting of an alkyl group, alkoxyl group, nitro group, and halogen atom;
• wherein said 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:
• ##STR15## wherein R.sup.1 and R.sup.2 are as defined above;
• and wherein said thienoimidazole represented by formula (1) is added to said 1,4-dihalogenodimagnesium butane either directly or in a cake state or slurry state, wherein said 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 said reaction mixture obtained in step (a) with carbon dioxide to produce a reaction liquid;
• and
• (c) followed by hydrolyzing and dehydrating the reaction liquid.