Benzyl Bromide → HCID 178482717, compound

HRID 230390Notes

Reaction equation

HRID 230390 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]([CH2:12][NH:13][CH3:14])[NH:10][CH:11]=2)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C=O.O>[CH2:27]([N:13]([CH3:14])[CH2:12][C:9]1[NH:10][CH:11]=[C:7]([C:4]2[CH:5]=[CH:6][C:1]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:2][CH:3]=2)[N:8]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178483028HCID 178483028, compound

Product 1

HCID 178482717HCID 178482717, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(4-(1,1′-biphenyl)-4-yl-1H-imidazol-2-yl)-N-methylmethanamine (1 g; 0.003 mol; prepared according to experimental conditions analogous to the preceding examples and using the appropriate starting compounds and reaction products) was diluted in 20 ml dimethylformamide. Potassium carbonate (1.23 g; 0.009 mol) was added at about 23° C. and then benzyl bromide (0.34 ml; 0.003 mol) was added quite slowly. The reaction mixture was agitated at this temperature for about 48 hours then poured in icy water. The mixture was extracted with ethyl acetate and the organic phase washed with water. After drying over magnesium sulfate, the solvents were concentrated using a rotative evaporator. After purification over a silica column (eluent: ethyl acetate-heptane/8-2), a white solid was obtained in the form of a glue (yield of 16%). Free base. Melting point: 106-108° C. MH+=354.2.

Workup

  1. customprepared
  2. customcompounds and reaction products)
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic phase washed with water
  5. dry with materialAfter drying over magnesium sulfate
  6. concentrationthe solvents were concentrated
  7. customa rotative evaporator
  8. customAfter purification over a silica column (eluent: ethyl acetate-heptane/8-2)
  9. customa white solid was obtained in the form of a glue (yield of 16%)

Sources & evidence

ORD record
ord-ce79e71f2a5b444a94c493894057f618
Source dataset
uspto-grants-2009_07
Patent number
US07566734B2

Reaction notes

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