Dimethyl Sulfoxide → 5-benzenesulfonyl-1-methyl-1H-imidazole-4-carbaldehyde

HRID 1944496Notes

Reaction equation

HRID 1944496 reaction equation
[Na+].[C:2]1([S:8]([O-:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:12]1[N:16]([CH3:17])[CH:15]=[N:14][C:13]=1[CH:18]=[O:19].CS(C)=O>C(OCC)(=O)C>[C:2]1([S:8]([C:12]2[N:16]([CH3:17])[CH:15]=[N:14][C:13]=2[CH:18]=[O:19])(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 2723840Benzenesulfinic acid, sodium salt2×HCID 127422785-bromo-1-methyl-1H-imidazole-4-carbaldehyde

Product 1

HCID 866522145-benzenesulfonyl-1-methyl-1H-imidazole-4-carbaldehydeYield 61.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of benzenesulfinic acid sodium salt (0.065 g), 5-bromo-1-methyl-1H-imidazole-4-carbaldehyde (0.037 g) and dimethyl sulfoxide (2.0 mL) was heated by microwave irradiation at 180° C. for 10 minutes. The mixture was treated with additional benzenesulfinic acid sodium salt (0.065 g), and heated by microwave irradiation at 180° C. for 40 minutes. The mixture was diluted with ethyl acetate, washed with water and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was triturated with cyclohexane to afford a yellow solid. The solid was collected by filtration, washed with cyclohexane and dried to afford the title compound (0.030 g).

Workup

  1. temperatureheated by microwave irradiation at 180° C. for 40 minutes
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was triturated with cyclohexane
  6. customto afford a yellow solid
  7. filtrationThe solid was collected by filtration
  8. washwashed with cyclohexane
  9. customdried

Sources & evidence

ORD record
ord-3fbf8903b7da4cb3875cfe3b5be1b0ca
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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