N'-hydroxyfuran-2-carboximidamide

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-chloro-2-methylbenzaldehyde (229 mg, 1.49 mmol), N′-hydroxyfuran-2-carboximidamide (263 mg, 2.1 mmol) and one drop of piperidine was heated to 100° C. for 4 h. It was cooled to RT and purified by automated column chromatography on the ISCO-companion (SiO2, gradient heptane/ethyl acetate) to give the 5-(4-chloro-2-methylphenyl)-3-(furan-2-yl)-4,5-dihydro-1,2,4-oxadiazole product (94 mg, 0.36 mmol) as an off-white solid with an HPLC purity 99%. The overall yield was approximately 24%. LC-MS [M+H] 263 (C13H11ClN2O2+H, expected 263.05). It was cooled to RT purified by automated column chromatography on the ISCO-companion (SiO2, gradient heptane/ethyl acetate)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-chloro-2-methylbenzaldehyde (229 mg, 1.49 mmol), N′-hydroxyfuran-2-carboximidamide (263 mg, 2.1 mmol) and one drop of piperidine was heated to 100° C. for 4 h. It was cooled to RT and purified by automated column chromatography on the ISCO-companion (SiO2, gradient heptane/ethyl acetate) to give the 5-(4-chloro-2-methylphenyl)-3-(furan-2-yl)-4,5-dihydro-1,2,4-oxadiazole product (94 mg, 0.36 mmol) as an off-white solid with an HPLC purity 99%. The overall yield was approximately 24%. LC-MS [M+H] 263 (C13H11ClN2O2+H, expected 263.05). It was cooled to RT purified by automated column chromatography on the ISCO-companion (SiO2, gradient heptane/ethyl acetate)

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

Procedure: To a solution of 2-furanamidoxime (12.6 g, 0.1 mole) and p-nitrobenzoyl chloride (18.1 g, 0.1 mole) in 500 ml of dry dioxane, 1 ml of BF3 -ethyl ether is added and the mixture is heated to reflux for 16 hours. Evaporation of the solvent in vacuo gives a light brown solid. It is decolorized with Darco (CHCl3) and crystallized from ethanol-acetonitrile to give 19.2 g (75%) of product, m.p. 168°-170°. the mixture is heated to reflux for 16 hours Evaporation of the solvent in vacuo gives a light brown solid crystallized from ethanol-acetonitrile

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

Procedure: To a solution of 2-furanamidoxime (12.6 g, 0.1 mole) and p-nitrobenzoyl chloride (18.1 g, 0.1 mole) in 500 ml of dry dioxane, 1 ml of BF3 -ethyl ether is added and the mixture is heated to reflux for 16 hours. Evaporation of the solvent in vacuo gives a light brown solid. It is decolorized with Darco (CHCl3) and crystallized from ethanol-acetonitrile to give 19.2 g (75%) of product, m.p. 168°-170°. the mixture is heated to reflux for 16 hours Evaporation of the solvent in vacuo gives a light brown solid crystallized from ethanol-acetonitrile

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

Procedure: To a solution of 2-furanamidoxime (12.6 g, 0.1 mole) and p-nitrobenzoyl chloride (18.1 g, 0.1 mole) in 500 ml of dry dioxane, 1 ml of BF3 -ethyl ether is added and the mixture is heated to reflux for 16 hours. Evaporation of the solvent in vacuo gives a light brown solid. It is decolorized with Darco (CHCl3) and crystallized from ethanol-acetonitrile to give 19.2 g (75%) of product, m.p. 168°-170° . the mixture is heated to reflux for 16 hours Evaporation of the solvent in vacuo gives a light brown solid crystallized from ethanol-acetonitrile

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-chloro-2-methylbenzaldehyde (229 mg, 1.49 mmol), N′-hydroxyfuran-2-carboximidamide (263 mg, 2.1 mmol) and one drop of piperidine was heated to 100° C. for 4 h. It was cooled to RT and purified by automated column chromatography on the ISCO-companion (SiO2, gradient heptane/ethyl acetate) to give the 5-(4-chloro-2-methylphenyl)-3-(furan-2-yl)-4,5-dihydro-1,2,4-oxadiazole product (94 mg, 0.36 mmol) as an off-white solid with an HPLC purity 99%. The overall yield was approximately 24%. LC-MS [M+H] 263 (C13H11ClN2O2+H, expected 263.05). It was cooled to RT purified by automated column chromatography on the ISCO-companion (SiO2, gradient heptane/ethyl acetate)

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

Procedure: To a solution of 2-furanamidoxime (12.6 g, 0.1 mole) and p-nitrobenzoyl chloride (18.1 g, 0.1 mole) in 500 ml of dry dioxane, 1 ml of BF3 -ethyl ether is added and the mixture is heated to reflux for 16 hours. Evaporation of the solvent in vacuo gives a light brown solid. It is decolorized with Darco (CHCl3) and crystallized from ethanol-acetonitrile to give 19.2 g (75%) of product, m.p. 168°-170°. the mixture is heated to reflux for 16 hours Evaporation of the solvent in vacuo gives a light brown solid crystallized from ethanol-acetonitrile