4-Fluorobenzonitrile → 4-[n-(1h-Imidazol-1-yl)-n-(4-trifluoromethylphenyl)amino]benzonitrile

HRID 1582612Notes

Reaction equation

HRID 1582612 reaction equation
C(O[K])(C)(C)C.[N:7]1([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[CH:11]=[CH:10][N:9]=[CH:8]1.N1C=CNC1=S.F[C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=1.[Na]>CS(C)=O.O>[N:7]1([N:12]([C:30]2[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=2)[C:13]2[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=2)[CH:11]=[CH:10][N:9]=[CH:8]1

Participants

8

Reactant 5

HCID 145174-FluorobenzonitrileHCID 12013862-MercaptoimidazoleHCID 5360545SodiumHCID 12985732N-(1H-imidazol-1-yl)-4-trifluoromethylanilineHCID 178418922HCID 178418922, compound

Product 1

HCID 103144104-[n-(1h-Imidazol-1-yl)-n-(4-trifluoromethylphenyl)amino]benzonitrileYield 63%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

To a cold solution (10-15° C.) of tBuOK (1.06 g, 0.00895 mol) in DMSO (18 ml) was added portionwise N-(1H-imidazol-1-yl)-4-trifluoromethylaniline (1.85 g, 0.00814 mol) (prepared by desulfurization from the corresponding 2,3-dihydro-1H-imidazol-2-thione, J. G. Schantl, Heterocycles, 37(3), 1873, 1994). The reaction mixture was stirred at room temperature for 1 h, then 4-fluorobenzonitrile (0.936 g, 0.00773 mol) in DMSO (18 ml) was added, the reaction mixture was stirred for 2 h and pourred into water and concentrated sodium hydroxyde solution. The precipitate was collected and dried under vacuum. Flash chromatography on silica gel (toluene/dioxane: 7/3) and crystallization from diisopropyl ether yielded a solid (1.6 g, 60%), mp 104° C.

Workup

  1. stirringthe reaction mixture was stirred for 2 h
  2. customThe precipitate was collected
  3. customdried under vacuum
  4. customFlash chromatography on silica gel (toluene/dioxane: 7/3) and crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-58166f99933d4747a386a5e98ab7980e
Source dataset
uspto-grants-2004_05
Patent number
US06737433B1

Reaction notes

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