5-Nitrofurfural → HCID 178463008, compound

HRID 515428Notes

Reaction equation

HRID 515428 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][CH3:21])[N:15]=3)[CH2:10][CH2:9]2)=[C:4]([F:22])[CH:3]=1.[N+:23]([C:26]1[O:30][C:29]([CH:31]=O)=[CH:28][CH:27]=1)([O-:25])=[O:24]>CC(O)=O.CO>[CH2:20]([N:16]1[N:15]=[C:14]([CH:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:6]=[CH:7][C:2](/[N:1]=[CH:31]/[C:29]4[O:30][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=4)=[CH:3][C:4]=3[F:22])[CH2:9][CH2:10]2)[O:18][C:17]1=[O:19])[CH3:21]

Participants

5

Reactant 2

HCID 127745-NitrofurfuralHCID 896482695-[1-(4-Amino-2-fluorophenyl)-4-piperidyl]-3-ethyl-2,3-dihydro-1,3,4-oxadiazol-2-one

Product 1

HCID 178463008HCID 178463008, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

5-[1-(4-Amino-2-fluorophenyl)-4-piperidyl]-3-ethyl-2,3-dihydro-1,3,4-oxadiazol-2-one (7 g, 0.30 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 re-crystallized in ethanol to obtain product 3-ethyl-5-[1-(2-fluoro-4-[(E)-1-(5-nitro-2-furyl)methylidene]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (9 g, 373 mg, 87%).

Workup

  1. filtrationthe obtained solid is filtered
  2. washwashed with water
  3. customre-crystallized in ethanol

Sources & evidence

ORD record
ord-d4c48bb4b5294571ac8f57d31b79872e
Source dataset
uspto-grants-2015_08
Patent number
US09108960B2

Reaction notes

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