2,4-Difluoronitrobenzene → 2-(5-Fluoro-2-nitro-phenylamino)-thiophene-3-carbonitrile

HRID 131380

Reaction equation

HRID 131380 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][C:13]1[S:14][CH:15]=[CH:16][C:17]=1[C:18]#[N:19].O.[OH-].[Li+]>CS(C)=O>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:12][C:13]2[S:14][CH:15]=[CH:16][C:17]=2[C:18]#[N:19])[CH:7]=1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 168937Lithium hydroxide, monohydrateHCID 7366072-Aminothiophene-3-carbonitrile

Product 1

HCID 692118502-(5-Fluoro-2-nitro-phenylamino)-thiophene-3-carbonitrileYield 45%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Combine 2,4-difluoro-1-nitro-benzene (5.24 g, 32.94 mmol), 2-aminothiophene-3-carbonitrile (4.09 g, 32.94 mmol), and DMSO (30.0 ml). Add lithium hydroxide monohydrate (2.76 g, 65.88 mmol) all at once and then stir the mixture at 55° for 22 hours. Cool the mixture to ambient temperature and then pour it onto ice chips. Extract with ethyl acetate and then wash (brine), dry (sodium sulfate), and evaporate the organic to residue. Purify the residue on silica gel using hexanes/dichloromethane (35:65) to give 3.89 g (45%) of the title compound as a red solid: mass spectrum (ion spray): m/z=262.0 (M−1).

Workup

  1. additionpour it onto ice chips
  2. extractionExtract with ethyl acetate
  3. washwash (brine)
  4. dry with materialdry (sodium sulfate)
  5. customevaporate the organic to residue
  6. customPurify the residue on silica gel

Sources & evidence

ORD record
ord-2c4b8a4f82994450bcaa96a83066b968
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Linked notes

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