2,5-Difluoronitrobenzene → 2-(4-Fluoro-2-nitro-phenylamino)-5-isopropyl-benzonitrile

HRID 131323

Reaction equation

HRID 131323 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][C:3]=1[C:4]#[N:5].F[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22].O.[OH-].[Li+]>CS(C)=O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([NH:1][C:2]2[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][C:3]=2[C:4]#[N:5])=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=1

Participants

5

Reactant 3

HCID 677672,5-DifluoronitrobenzeneHCID 168937Lithium hydroxide, monohydrateHCID 210934632-Amino-5-isopropylbenzonitrile

Product 1

HCID 210934592-(4-Fluoro-2-nitro-phenylamino)-5-isopropyl-benzonitrileYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Heat a solution of 2-amino-5-isopropyl-benzonitrile (1.482 g, 9.25 mmol) with 1,4-difluoro-2-nitro-benzene (1.47 g, 9.25 mmol) and lithium hydroxide monohydrate (0.78 g, 18.50 mmol) in DMSO (20 ml) to 70° C. for 38 hours. Cool the reaction to ambient temperature and pour into approximately 200 ml of ice water and stir for one hour. Collect by filtration the title compound which precipitates. No further purification is necessary to obtain 2.236 g (7.47 mmol, 81% yield) of the title compound as an orange amorphous solid: Mass Spectrum (m/e): 300(M+1).

Workup

  1. temperatureCool
  2. customthe reaction to ambient temperature
  3. filtrationCollect by filtration the title compound which
  4. customprecipitates
  5. customNo further purification

Sources & evidence

ORD record
ord-6582b858a7dc4b12a586e38b3ad3f56b
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Linked notes

Loading…