Furfural → HCID 178478004, compound

HRID 589292Notes

Reaction equation

HRID 589292 reaction equation
[CH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[O:3][CH:2]=1.[Cl:8][C:9]1[CH:18]=[CH:17][C:12]([C:13](=[N:15]O)[NH2:14])=[CH:11][CH:10]=1>N1CCCCC1.C1(C)C=CC=CC=1>[Cl:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]2[NH:15][CH:6]([C:4]3[O:3][CH:2]=[CH:1][CH:5]=3)[O:7][N:14]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 7362FurfuralHCID 2246504-chloro-N'-hydroxybenzenecarboximidamide

Product 1

HCID 178478004HCID 178478004, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-furfural (0.69 mL, 804 mg, 8.4 mmol), 4-chloro-N′-hydroxybenzimidamide (1.02 g, 6.0 mmol) and one drop of piperidine in toluene (100 mL) was heated to reflux for 18 h in a Soxhlett apparatus, that was charged with 3 Angstrom molecular sieves (8 g). The mixture was cooled to room temperature and the solvent was removed in vacuo. After purification by automated column chromatography on the ISCO COMPANION (SiO2, gradient heptane/ethyl acetate) the 3-(4-chlorophenyl)-5-(furan-2-yl)-4,5-dihydro-1,2,4-oxadiazole product was obtained as an orange oil that solidified to a tan solid upon standing (85 mg) with a yield of 6%. LC-MS [M+H] 249 (C12H9ClN2O2+H, expected 249.04)

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 h in a Soxhlett apparatus, that
  3. additionwas charged with 3 Angstrom molecular sieves (8 g)
  4. customthe solvent was removed in vacuo
  5. customAfter purification by automated column chromatography on the ISCO COMPANION (SiO2, gradient heptane/ethyl acetate) the 3-(4-chlorophenyl)-5-(furan-2-yl)-4,5-dihydro-1,2,4-oxadiazole product
  6. customwas obtained as an orange oil that solidified to a tan solid

Sources & evidence

ORD record
ord-f1b44d96ac2b47dda235902838075f0f
Source dataset
uspto-grants-2016_01
Patent number
US09232800B2

Reaction notes

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