5-Nitrofurfural → HCID 178518789, compound

HRID 515422Notes

Reaction equation

HRID 515422 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[O:18][C:17](=[O:19])[NH:16][N:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[N+:20]([C:23]1[O:27][C:26]([CH:28]=O)=[CH:25][CH:24]=1)([O-:22])=[O:21]>CC(O)=O.CO>[N+:20]([C:23]1[O:27][C:26](/[CH:28]=[N:1]/[C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:9][CH2:10][CH:11]([C:14]4[O:18][C:17](=[O:19])[NH:16][N:15]=4)[CH2:12][CH2:13]3)=[CH:6][CH:7]=2)=[CH:25][CH:24]=1)([O-:22])=[O:21]

Participants

5

Reactant 2

HCID 127745-NitrofurfuralHCID 896504445-[1-(4-Aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one

Product 1

HCID 178518789HCID 178518789, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

5-[1-(4-Aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (7a, 0.26 g, 1 mmol) on reacting with 5-nitro2-furaldehyde in the presence of catalytic amount of CH3COOH (3 drops) in methanol at 0° C. for 10 h and the obtained solid is filtered, washed with water and recrystallized in ethanol to obtain product 5-[1-(4-[(E)-1-(5-nitro-2-furyl)methylidene]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (9a, 306 mg, 80%).

Workup

  1. filtrationthe obtained solid is filtered
  2. washwashed with water
  3. customrecrystallized in ethanol

Sources & evidence

ORD record
ord-94301df291484a8eb9b84e9c79c824d6
Source dataset
uspto-grants-2015_08
Patent number
US09108960B2

Reaction notes

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