Triethylamine → (E)-3-[4,5-Bis(4-fluorophenyl)-2-trifluoromethyl-1H-imidazol-1-yl]-2-propenenitrile

HRID 2050571Notes

Reaction equation

HRID 2050571 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:20]([F:23])([F:22])[F:21])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.Br[CH:25]([CH2:28]Br)[C:26]#[N:27].C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C>CN(C=O)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:11]=[C:10]([C:20]([F:22])([F:21])[F:23])[N:9](/[CH:28]=[CH:25]/[C:26]#[N:27])[C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 1072992,3-DibromopropanenitrileHCID 148497684,5-bis(4-fluorophenyl)-2-trifluoromethyl-1H-imidazole

Product 1

HCID 14849771(E)-3-[4,5-Bis(4-fluorophenyl)-2-trifluoromethyl-1H-imidazol-1-yl]-2-propenenitrileYield 41.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

From 4,5-bis(4-fluorophenyl)-2-trifluoromethyl-1H-imidazole (3.045 g), 2,3-dibromopropionitrile (5.33 g), anhydrous potassium carbonate (3.1 g) and triethylamine (5.2 ml) in dry DMF (19 ml) by the process as described for the preparation of Intermediate (3 a) to afford a dark brown residue which was purified by FCC using gradient elution with System A (5-15% with 5% incremental increase of ethyl acetate per 500 ml eluant) to afford the title compound (1.449 g) as a white solid. νmax (CHBr3) 2229 cm-1 (C≡N).

Workup

  1. customto afford a dark brown residue which
  2. customwas purified by FCC
  3. washelution with System
  4. temperatureA (5-15% with 5% incremental increase of ethyl acetate per 500 ml eluant)

Sources & evidence

ORD record
ord-77f3e7037c994882a79678f90e35ca2f
Source dataset
uspto-grants-1991_05
Patent number
US05013749

Reaction notes

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