Furfural → HCID 178420175, compound

HRID 589291Notes

Reaction equation

HRID 589291 reaction equation
[CH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[O:3][CH:2]=1.O[N:9]=[C:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1CCCCC1.C1(C)C=CC=CC=1>[O:3]1[CH:2]=[CH:1][CH:5]=[C:4]1[CH:6]1[O:7][N:9]=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:17]1

Participants

5

Reactant 2

HCID 7362FurfuralHCID 69186N'-Hydroxybenzenecarboximidamide

Product 1

HCID 178420175HCID 178420175, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-furfural (1.0 mL, 1.17 g, 12.2 mmol, 1.5 equivalents), N′-hydroxybenzimidamide (1.11 g, 8.1 mmol) and one drop of piperidine in toluene (100 mL) was heated to reflux for 18 hours in a SOXHLETT apparatus that was charged with SILCARBON 3 Angstrom molecular sieve (8 g). The reaction mixture was allowed to cool to room temperature, and the solvent was removed in vacuo. After purification by automated column chromatography on an ISCO COMPANION apparatus (SiO2, gradient heptane/ethyl acetate), the 5-(furan-2-yl)-3-phenyl-4,5-dihydro-1,2,4-oxadiazole product (745 mg, 3.5 mmol) was obtained as a brown oil that solidified to a tan solid upon standing. The overall reaction yield was approximately 43%. LC-MS [M+H] 215 (C12H10N2O2+H, expected 215.07].

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours in a SOXHLETT apparatus that
  3. additionwas charged with SILCARBON 3 Angstrom molecular sieve (8 g)
  4. customthe solvent was removed in vacuo
  5. customAfter purification by automated column chromatography on an ISCO COMPANION apparatus (SiO2, gradient heptane/ethyl acetate)

Sources & evidence

ORD record
ord-13b71fcdc0e74ce5a651b1bb185fc890
Source dataset
uspto-grants-2016_01
Patent number
US09232800B2

Reaction notes

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