Triethylamine → N-cyclopentyl-2-methylfuran-3-hydroxamic acid

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Reaction Steps

30 Parts of triethylamine is added to a suspension of 20 parts of N-cyclopentylhydroxylamine hydrochloride in 300 parts of benzene and the whole is stirred for 1 hour. At room temperature, 10 parts of 2-methylfuran-3-carboxylic chloride is dripped in. After the mixture has been stirred for a further 3 hours it is suction filtered, the residue is washed with benzene, and the organic phase is washed with water, dried with sodium sulfate and evaporated. There is obtained 25 parts of N-cyclopentyl-2-methylfuran-3-hydroxamic acid in the form of an oil. This oil is dissolved in 300 parts of dichloromethane; while stirring and at room temperature, 16 parts of sodium hydroxide in 70 parts of water, and 26 parts of dimethyl sulfate are added to the solution. After the mixture has been stirred for 2 hours the organic phase is separated, washed with water until neutral and dried with anhydrous sodium sulfate. Distillation gives 21 parts of O-methyl-N-cyclopentyl-2-methylfuran- 3-hydroxamic acid having a boiling point at 0.01 mm Hg of 104° to 108° C and the refractive index nD25 : 1.5073. ##SPC14##

Provenance & Evidence