4-Fluoro-2-nitroaniline → 2-(4-Fluoro-2-nitro-phenylamino)-5-trifluoromethyl-benzonitrile

HRID 1350532Notes

Reaction equation

HRID 1350532 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.F[C:13]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:14]=1[C:15]#[N:16].O.[OH-].[Li+]>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:13]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:24])[F:23])=[CH:17][C:14]=2[C:15]#[N:16])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 677694-Fluoro-2-nitroanilineHCID 168937Lithium hydroxide, monohydrateHCID 5210162-Fluoro-5-(trifluoromethyl)benzonitrile

Product 1

HCID 210934612-(4-Fluoro-2-nitro-phenylamino)-5-trifluoromethyl-benzonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

Combine 4-fluoro-2-nitro-phenylamine (5.9 g, 32.03 mmol), 2-fluoro-5-trifluoromethyl-benzonitrile (6.07 g, 32.03 mmol) and lithium hydroxide monohydrate (4.03 g, 96.08 mmol) in methyl sulfoxide (DMSO, 60 ml). Heat the resulting mixture to 70° C. for 16 hours. Cool the reaction mixture to ambient temperature, then pour into approximately 400 ml of ice water and stir for one hour. Filter the resulting mixture and collect the precipitate. Obtained 9.995 g of the title compound (30.73 mmol, 96% yield) as an orange amorphous solid. Product used as is with no further purification: Mass Spectrum (m/e): 326(M+1).

Workup

  1. temperatureCool the reaction mixture to ambient temperature
  2. filtrationFilter the resulting mixture
  3. customcollect the precipitate

Sources & evidence

ORD record
ord-9a2c154e4e474f98ae0e5c4b9c390ee0
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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