Process for producing 5-substituted oxazole compounds and 5-substituted imidazole compounds
AssigneeNippon Soda Co., Ltd.
InventorsAtsushi Ogihara, Hiroshi Sakai, Nobuo Matsui, Hidekazu Miyazaki
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Abstract
A process for producing heterocyclic compounds which are useful as pesticides, drugs, fungicidal materials or intermediates thereof. TosMIC is reacted with an aldehyde or an imino compound: 1) in a solvent mixture of an aprotic solvent with a protic solvent in the presence of a base, 2) in the presence of a phase-transfer catalyst and an inorganic base, or 3) in the presence of an inorganic base. Thus, a desired product can be efficiently obtained using a solution without isolating TosMIC which is irritating and unstable, has a low decomposition point and shows explosivity.
Claims8
A process for the preparation of a 5-substituted oxazole or 5-substituted imidazole comprising
- synthesizing p-tolylsulfonylmethylisocyanide from N-(p-tolylsulfonylmethyl)formamide with phosphorus oxychloride, phosgene or diphosgene, and a tertiary amine, to form a p-tolylsulfonylmethylisocyanide solution which is not isolated and purified as crystals,
- washing the p-tolylsulfonylmethylisocyanide solution with an aqueous alkaline solution, and
- reacting the p-tolylsulfonylmethylisocyanide solution with an aldehyde or a compound represented by Formula (I):
- R1CH═NR2
- wherein, R1 and R2 are optionally substituted phenyl, optionally substituted heterocyclic group or optionally substituted alkyl,
- wherein the p-tolylsulfonylmethylisocyanide solution is reacted with an aldehyde or a compound of Formula (I) in a mixed solvent of an aprotic solvent and a protic solvent in the presence of potassium hydroxide or sodium hydroxide or mixtures thereof.
A process for the preparation of a 5-substituted oxazole or 5-substituted imidazole comprising
- synthesizing p-tolylsulfonylmethylisocyanide from N-(p-tolylsulfonylmethyl) formamide with phosphorus oxychloride, phosgene or diphosgene, and a tertiary amine, to form a p-tolylsulfonylmethylisocyanide solution which is not isolated and purified as crystals,
- washing the p-tolylsulfonylmethylisocyanide solution with an aqueous alkaline solution, and
- reacting the p-tolylsulfonylmethylisocyanide solution with an aldehyde or a compound represented by Formula (I):
- R1CH═NR2
- wherein, R1 and R2 are optionally substituted phenyl, optionally substituted heterocyclic group or optionally substituted alkyl,
- wherein the aldehyde or the compound of Formula [I] is reacted with p-tolylsulfonylmethylisocyanide in a mixed solvent of an aprotic solvent and water in the presence of an inorganic base and between about 0.0001 moles and about 5 moles of at least one phase-transfer catalyst selected from the group consisting of quaternary ammonium salts and salts, quaternary phosphonium salts and an inorganic base, salts, crown compounds and organic bases.
A process for the preparation of a 5-substituted oxazole or 5-substituted imidazole comprising
- synthesizing p-tolylsulfonylmethylisocyanide from N-(p-tolylsulfonylmethyl) formamide with phosphorus oxychloride, phosgene or diphosgene, and a tertiary amine, to form a p-tolylsulfonylmethylisocyanide solution which is not isolated and purified as crystals,
- washing the p-tolylsulfonylmethylisocyanide solution with an aqueous alkaline solution, and
- reacting the p-tolylsulfonylmethylisocyanide solution with an aldehyde or a compound represented by Formula (I):
- R1CH═NR2
- wherein, R1 and R2 are optionally substituted phenyl, optionally substituted heterocyclic group or optionally substituted alkyl,
- wherein the aldehyde or the compound of Formula [I] is reacted with p-tolylsulfonylmethylisocyanide in halogen-type solvents, aromatic hydrocarbon-type solvents, ester-type solvents, ketone-type solvents, ether-type solvents, or polar solvents in the presence of an organic base which has a pKa of 12 or more.
Dependencies are inferred from the claim text.