5-Nitrofurfural → HCID 178519066, compound

HRID 515429Notes

Reaction equation

HRID 515429 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]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:15]=3)[CH2:10][CH2:9]2)=[C:4]([F:27])[CH:3]=1.[N+:28]([C:31]1[O:35][C:34]([CH:36]=O)=[CH:33][CH:32]=1)([O-:30])=[O:29]>CC(O)=O.CO>[CH2:20]([N:16]1[N:15]=[C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:5]3[CH:6]=[CH:7][C:2](/[N:1]=[CH:36]/[C:34]4[O:35][C:31]([N+:28]([O-:30])=[O:29])=[CH:32][CH:33]=4)=[CH:3][C:4]=3[F:27])[CH2:13][CH2:12]2)[O:18][C:17]1=[O:19])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 127745-NitrofurfuralHCID 896505625-[1-(4-Amino-2-fluorophenyl)-4-piperidyl]-3-benzyl-2,3-dihydro-1,3,4-oxadiazol-2-one

Product 1

HCID 178519066HCID 178519066, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

5-[1-(4-Amino-2-fluorophenyl)-4-piperidyl]-3-benzyl-2,3-dihydro-1,3,4-oxadiazol-2-one (7 h, 0.36 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-benzyl-5-[1-(2-fluoro-4-[(E)-1-(5-nitro-2-furyl)methylidene]amino phenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (9 h, 432 mg, 88%).

Workup

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

Sources & evidence

ORD record
ord-1994dccc66274cea9f022cac792f1667
Source dataset
uspto-grants-2015_08
Patent number
US09108960B2

Reaction notes

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