FIELD: organic chemistry.
SUBSTANCE: invention relates to a method for producing 1-methyl-N-aryl-3-oxo-8-phenyl-2-oxa-6-thia-bicyclo[2.2.2]octane-5-carboxamides of formula (2)
where R=4-СН3С6Н4, 4-СН3ОС6Н4, 4-НОС6Н4, 4-ClC6H4, 4-BrC6H4, СН2С6Н5. The method includes one stage of the reaction, isolation of the target products by filtering the precipitate and its further purification by recrystallization from glacial acetic acid. When carrying out the synthesis, a solution of 2-[arylcarbamoyl]-6-methyl-4-phenyl-3,4-dihydro-2H-thiopyran-3-carboxylic acid in a solvent is prepared. The solvent used is carbon tetrachloride, chloroform or dichloromethane. Next, an acid selected from sulfuric, hydrochloric, phosphoric, acetic or trifluoroacetic is added to the resulting solution in a molar ratio from 5 to 110%. The reaction mixture is stirred at a temperature from 40 to 77°C for 1 to 3 hours. The precipitate that formed was 1-methyl-N-aryl-3-oxo-8-phenyl-2-oxa-6-thia-bicyclo[2.2.2]octane-5-carboxamide (2) filter and wash with the same solvent. The product is recrystallized from glacial acetic acid.
EFFECT: method for the synthesis of new 1-methyl-N-aryl-3-oxo-8-phenyl-2-oxa-6-thia-bicyclo[2.2.2]octane-5-carboxamides (2), using available reagents.
1 cl, 1 tbl, 6 ex
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