4-Toluenesulfonyl chloride → 5-methyl-1-tosyl-1H-imidazole-4-carbaldehyde

HRID 486219

Reaction equation

HRID 486219 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH:7]=[O:8].C(N(CC)CC)C.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>CN(C)C=O.O.CO>[CH3:1][C:2]1[N:6]([S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])[CH:5]=[N:4][C:3]=1[CH:7]=[O:8]

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 27958875-Methyl-1H-imidazole-4-carbaldehyde

Product 1

HCID 150519515-methyl-1-tosyl-1H-imidazole-4-carbaldehydeYield 83.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-methyl-1H-imidazole-4-carbaldehyde (20 g) in N,N-dimethylformamide (100 ml) was added triethylamine (20.5 g) and p-toluenesulfonyl chloride (38 g). The mixture was stirred under ice-cooling for two hours. The reaction mixture was diluted with water (600 ml) and separated organic layer was filtered. The residue obtained was suspended in methanol (100 ml). After being stirred at ambient temperature for two hours, the mixture was cooled and filtered to give 5-methyl-1-tosyl-1H-imidazole-4-carbaldehyde (40.3 g).

Workup

  1. temperaturecooling for two hours
  2. customseparated organic layer
  3. filtrationwas filtered
  4. customThe residue obtained
  5. stirringAfter being stirred at ambient temperature for two hours
  6. temperaturethe mixture was cooled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-da4887896f4b4fe3b48ad314ed9cc3a3
Source dataset
uspto-grants-1994_03
Patent number
US05290785

Linked notes

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