Furfural → HCID 178426101, compound

HRID 589293Notes

Reaction equation

HRID 589293 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].[Cl:8][C:9]1[CH:18]=[CH:17][C:12]([C:13](=[N:15]O)[NH2:14])=[C:11]([CH3:19])[CH:10]=1>N1CCCCC1>[Cl:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]2[NH:15][CH:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[O:7][N:14]=2)=[C:11]([CH3:19])[CH:10]=1

Participants

4

Reactant 2

HCID 7362FurfuralHCID 51521484-Chloro-N-hydroxy-2-methylbenzamidine

Product 1

HCID 178426101HCID 178426101, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Conditions

Temperature
10 °C

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)

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompurified by automated column chromatography on the ISCO COMPANION (SiO2, gradient heptanes/ethyl acetate)

Sources & evidence

ORD record
ord-21a42dd58c2249dc83c587efe413fbc4
Source dataset
uspto-grants-2016_01
Patent number
US09232800B2

Reaction notes

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