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(Process (a)) 2.52 g (0.02 mol) of 5-methyl-isoxazole-3-carboxamide are dissolved in 50 ml of 1,4-dioxane and after adding 3.4 g (0.06 mol) of powdered potassium hydroxide the mixture is stirred at 80 C. for 30 minutes. The mixture is cooled, 5.7 g (0.022 mol) of methyl 2-chlorosulphonylbenzoate are added at room temperature (20 C.) and the mixture is then stirred at room temperature for 20 hours. The solvent is then distilled off in vacuo, the residue is taken up in water and the solution is filtered. The product precipitates from the filtrate on acidifying with hydrochloric acid, and is collected on a suction filter and dried on clay. 1.8 g (27% of theory) of N-(2-methoxycarbonylphenylsulphonyl)-5-methyl-isoxazole-3-carboxamide of melting point 101 C. are obtained.
With potassium hydroxide; In 1,4-dioxane; water;
EXAMPLE 1 STR80 2.52 g (0.02 mol) of 5-methyl-isoxazole-3-carboxamide are dissolved in 50 ml of 1,4-dioxane and after adding 3.4 g (0.06 mol) of powdered potassium hydroxide the mixture is stirred at 80 C. for 30 minutes. The mixture is cooled, 5.7 g (0.022 mol) of methyl 2-chlorosulphonylbenzoate are added at room temperature for 20 hours. The solvent is then distilled off in vacuo, the residue is taken up in water and the solution is filtered. The product precipitates from the filtrate on acidifying with hydrochloric acid, and is collected on a suction filter and dried on clay. 1.8 g (27% of theory) of N-(2-methoxycarbonylphenylsulphonyl)-5-methyl-isoxazole-3-carboxamide of melting point 101 C. are obtained.
With pyridine; In ethanol; at 20℃; for 16.0h;Reflux;
5-Ethyl-2-(5-methyl-isoxazol-3-yl)-thiazol-4-ol: To a stirred solution of <strong>[3445-52-1]5-methyl-isoxazole-3-carbothioic acid amide</strong> (0.300 g, 2.11 mmol) and 2-bromo-butyric acid ethyl ester (0.0.37 mL, 2.53 mmol) in ethanol (10 mL) was added pyridine (0.29 mL, 3.59 mmol) at rt. The mixture was refluxed for 16 h (monitoring by TLC; ethyl acetate-hexane=3:7; Rf?0.3) before being concentrated under reduce pressure. The crude material was then redissolved in MeOH and diethyl ether which caused the precipitation of pure 5-ethyl-2-(5-methyl-isoxazol-3-yl)-thiazol-4-ol (0.430 g, crude) that was isolated as a brown sticky solid. LC-MS: 197 [M+H].
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