Dimethylformamide → HCID 67975261, compound

HRID 623940Notes

Reaction equation

HRID 623940 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CCOCC.O>[CH2:17]([N:12]1[CH:11]=[C:10]([C:13]([F:14])([F:16])[F:15])[N:9]=[C:8]1[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 534063902-(4-Bromophenyl)-5-(trifluoromethyl)-1H-imidazole

Product 1

HCID 67975261HCID 67975261, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-(4-bromophenyl)-5-(trifluoromethyl)-1H-imidazole (3 g), benzyl bromide (3.52 g), potassium carbonate (2.85 g) and N,N-dimethylformamide (30 mL) was stirred at room temperature overnight. To the reaction mixture were added water and ether, and the liquids were separated. The organic layer was separated, washed with water and then with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in toluene, and purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0 to 70:30) to obtain 1-benzyl-2-(4-bromophenyl)-4-(trifluoromethyl)-1H-imidazole (3.40 g).

Workup

  1. customthe liquids were separated
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialwith saturated brine, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe obtained residue was dissolved in toluene
  7. custompurified by silica gel column chromatography (n-hexane:ethyl acetate=100:0 to 70:30)

Sources & evidence

ORD record
ord-c41bf9995aff4d61aecc7721961c49f7
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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