Hydrochloric Acid → N-methyl-1-{1-[(4-methylphenyl)sulfonyl]-2-phenyl-1H-imidazol-4-yl}methanamine

HRID 2359959Notes

Reaction equation

HRID 2359959 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:15]=[C:14]([CH:16]=O)[N:13]=[C:12]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CO.[CH3:26][NH2:27].[BH4-].[Na+].Cl.C(=O)([O-])O.[Na+]>CO>[CH3:26][NH:27][CH2:16][C:14]1[N:13]=[C:12]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:11]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)(=[O:10])=[O:9])[CH:15]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 236606871-[(4-methylphenyl)sulfonyl]-2-phenyl-1H-imidazole-4-carbaldehydeHCID 57454252Monomethylamine methanol

Product 1

HCID 57687724N-methyl-1-{1-[(4-methylphenyl)sulfonyl]-2-phenyl-1H-imidazol-4-yl}methanamineYield 18.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[(4-Methylphenyl)sulfonyl]-2-phenyl-1H-imidazole-4-carbaldehyde (1.00 g) was dissolved in methanol (30 mL), 40% methylamine methanol solution (700 mg) was added at room temperature, and the mixture was stirred for 30 min. Sodium borohydride (171 mg) was added at 5-10° C., and the mixture was stirred for 30 min. 1 mol/L Hydrochloric acid was added at the same temperature, and the mixture was further stirred for 30 min. The reaction mixture was alkalified with saturated aqueous sodium hydrogen carbonate solution, 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:hexane-ethyl acetate=1:1→0:1), dissolved in ethyl acetate (10 mL), and crystallized by adding a solution (5 mL) of anhydrous oxalic acid (53 mg) in ethyl acetate to give the title compound as colorless crystals (yield 197 mg, 17%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. stirringthe mixture was further stirred for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→0:1)
  8. dissolutiondissolved in ethyl acetate (10 mL)
  9. customcrystallized
  10. additionby adding a solution (5 mL) of anhydrous oxalic acid (53 mg) in ethyl acetate

Sources & evidence

ORD record
ord-8fec8fa0751f44c68c5b847235e9f706
Source dataset
uspto-grants-2014_04
Patent number
US08686010B2

Reaction notes

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