4-chloro-N'-hydroxy-2-methylbenzenecarboximidamide

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-furancarboxaldehyde (166 mL, 192 mg, 2.0 mmol), 4-chloro-N′-hydroxy-2-methylbenzimidamide (368 mg, 2.0 mmol) and one drop of piperidine was heated to 10° C. for 4 h. The mixture was cooled to room temperature and purified by automated column chromatography on the ISCO COMPANION (SiO2, gradient heptanes/ethyl acetate) to give the 3-(4-chloro-2-methylphenyl)-5-(furan-2-yl)-4,5-dihydro-1,2,4-oxadiazole product (95 mg) with a yield of 18%. LC-MS [M+H] 263 (C13H11ClN2O2+H, expected 263.05) The mixture was cooled to room temperature purified by automated column chromatography on the ISCO COMPANION (SiO2, gradient heptanes/ethyl acetate)

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-furancarboxaldehyde (166 mL, 192 mg, 2.0 mmol), 4-chloro-N′-hydroxy-2-methylbenzimidamide (368 mg, 2.0 mmol) and one drop of piperidine was heated to 10° C. for 4 h. The mixture was cooled to room temperature and purified by automated column chromatography on the ISCO COMPANION (SiO2, gradient heptanes/ethyl acetate) to give the 3-(4-chloro-2-methylphenyl)-5-(furan-2-yl)-4,5-dihydro-1,2,4-oxadiazole product (95 mg) with a yield of 18%. LC-MS [M+H] 263 (C13H11ClN2O2+H, expected 263.05) The mixture was cooled to room temperature purified by automated column chromatography on the ISCO COMPANION (SiO2, gradient heptanes/ethyl acetate)