Nitrobenzene → 3-oxo-N-(4-(trifluoromethyl)phenyl)butanamide

HRID 1967637Notes

Reaction equation

HRID 1967637 reaction equation
[CH3:1]/[C:2](/[OH:19])=[C:3](/[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=1)=[O:7])\C#N.C(OC(=O)CC(C)=O)C.FC(F)(F)C1C=CC(N)=CC=1.[N+](C1C=CC=CC=1)([O-])=O>C1C=CC=CC=1.C1(C)C(C)=CC=CC=1.C1(C)C=CC=CC=1>[O:19]=[C:2]([CH3:1])[CH2:3][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=1)=[O:7]

Participants

8

Reactant 4

HCID 7416NitrobenzeneHCID 8868Ethyl AcetoacetateHCID 99644-(Trifluoromethyl)anilineHCID 54684141Teriflunomide

Product 1

HCID 14720783-oxo-N-(4-(trifluoromethyl)phenyl)butanamide

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 1140TolueneSolventHCID 7237O-XyleneSolvent

Procedure

The present invention provides a process for preparation of Teriflunomide. Ethylacetoacetate (II) and 4-trifluoromethyl aniline (III) is refluxed in a solvent. The solvent is selected from aromatic hydrocarbon such as toluene, xylene, nitrobenzene, benzene and the like or mixtures thereof. The reaction mixture is refluxed for about 48 hours. The Reaction mixture is concentrated and purified by column chromatography to give pure 3-oxo-N-(4-trifluoromethylphenyl)butanamide (IV).

Workup

  1. customThe present invention provides a process
  2. temperatureThe reaction mixture is refluxed for about 48 hours
  3. concentrationThe Reaction mixture is concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-f77ce566c0664db383322554239cb5d5
Source dataset
uspto-grants-2013_04
Patent number
US08420856B2

Reaction notes

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