5-Nitrofurfural → HCID 178481744, compound

HRID 515427Notes

Reaction equation

HRID 515427 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)=[C:4]([F:21])[CH:3]=1.[N+:22]([C:25]1[O:29][C:28]([CH:30]=O)=[CH:27][CH:26]=1)([O-:24])=[O:23]>CC(O)=O.CO>[F:21][C:4]1[CH:3]=[C:2](/[N:1]=[CH:30]/[C:28]2[O:29][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=2)[CH:7]=[CH:6][C:5]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:18][C:17](=[O:19])[N:16]([CH3:20])[N:15]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 127745-NitrofurfuralHCID 89650502HCID 89650502, compound

Product 1

HCID 178481744HCID 178481744, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

5-[1-(4-Amino-2-fluorophenyl)-4-piperidyl]-3-methyl-2,3-dihydro-1,3,4-oxadiazol-2-one (7f, 0.29 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-(2-fluoro-4-[(E)-1-(5-nitro-2-furyl)methylidene]aminophenyl)-4-piperidyl]-3-methyl-2,3-dihydro-1,3,4-oxadiazol-2-one (9f, 352 mg, 85%).

Workup

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

Sources & evidence

ORD record
ord-accb595d968148978d0b6c2f38e36e5d
Source dataset
uspto-grants-2015_08
Patent number
US09108960B2

Reaction notes

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