5-Nitrofurfural → HCID 178481743, compound

HRID 515423Notes

Reaction equation

HRID 515423 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])[N:16]([CH3:20])[N:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[N+:21]([C:24]1[O:28][C:27]([CH:29]=O)=[CH:26][CH:25]=1)([O-:23])=[O:22]>CC(O)=O.CO>[CH3:20][N:16]1[N:15]=[C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:5]3[CH:4]=[CH:3][C:2](/[N:1]=[CH:29]/[C:27]4[O:28][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][CH:26]=4)=[CH:7][CH:6]=3)[CH2:13][CH2:12]2)[O:18][C:17]1=[O:19]

Participants

5

Reactant 2

HCID 127745-NitrofurfuralHCID 896484465-[1-(4-Aminophenyl)-4-piperidyl]-3-methyl-2,3-dihydro-1,3,4-oxadiazol-2-one

Product 1

HCID 178481743HCID 178481743, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

5-[1-(4-Aminophenyl)-4-piperidyl]-3-methyl-2,3-dihydro-1,3,4-oxadiazol-2-one (7b, 0.27 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 3-methyl-5-[1-(4-[(E)-1-(5-nitro-2-furyl)methylidene]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (9b, 341 mg, 86%).

Workup

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

Sources & evidence

ORD record
ord-44902449bafa4aa5be65a56f645f6fdb
Source dataset
uspto-grants-2015_08
Patent number
US09108960B2

Reaction notes

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