Water → HCID 68410887, compound

HRID 2194718Notes

Reaction equation

HRID 2194718 reaction equation
Cl.Cl.[F:3][C:4]1[CH:24]=[CH:23][C:7]([CH2:8][N:9]2[CH:13]=[C:12]([CH2:14][NH:15][CH3:16])[N:11]=[C:10]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:6][CH:5]=1.[Cl:25]N1C(=O)CC[C:27]1=[O:32].[OH2:33].[C:34](=[O:37])([O-:36])O.[Na+]>CN(C)C=O>[C:27]([OH:32])(=[O:33])[C:34]([OH:36])=[O:37].[Cl:25][C:13]1[N:9]([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:24][CH:23]=2)[C:10]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:11][C:12]=1[CH2:14][NH:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 68409425HCID 68409425, compound

Product 1

HCID 68410887HCID 68410887, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[1-(4-fluorobenzyl)-2-phenyl-1H-imidazol-4-yl]-N-methylmethanamine dihydrochloride (100 mg) in dimethylformamide was added N-chlorosuccinimide (43 mg) and the mixture was stirred at room temperature for 3 hr. Water and saturated sodium hydrogen carbonate solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:ethyl acetate-methanol=19:1→3:2), a solution of oxalic acid (25 mg) in ethyl acetate (5 mL) was added, and the mixture was crystallized to give the title compound as colorless crystals (yield 20 mg, yield 18%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (eluent:ethyl acetate-methanol=19:1→3:2)
  6. additiona solution of oxalic acid (25 mg) in ethyl acetate (5 mL) was added
  7. customthe mixture was crystallized

Sources & evidence

ORD record
ord-e488e7b16b524d59a913ecb8f3be9443
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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