Water → 1-[(3-methoxyphenyl)sulfonyl]-2-phenyl-1H-imidazole-4-carbaldehyde

HRID 2359941Notes

Reaction equation

HRID 2359941 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([CH:12]=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([S:24](Cl)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1.O>O1CCCC1>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([S:24]([N:8]2[CH:9]=[C:10]([CH:12]=[O:13])[N:11]=[C:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27375043-Methoxybenzenesulfonyl chlorideHCID 178519858HCID 178519858, compound

Product 1

HCID 236606831-[(3-methoxyphenyl)sulfonyl]-2-phenyl-1H-imidazole-4-carbaldehydeYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-phenyl-1H-imidazole-4-carbaldehyde (520 mg) in tetrahydrofuran (100 mL) was added sodium hydride (60% in oil, 182 mg) at room temperature, and the mixture was stirred for 30 min. 3-Methoxybenzenesulfonyl chloride (750 mg) was added to the reaction mixture, and the mixture was stirred for 1.5 hr. Water was added, 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 crystallized from diethyl ether to give the title compound as colorless crystals (yield 894 mg, 87%).

Workup

  1. stirringthe mixture was stirred for 1.5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-fa17c2be8aaa46e6a544e447cad87bb2
Source dataset
uspto-grants-2014_04
Patent number
US08686010B2

Reaction notes

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