4-Toluenesulfonyl chloride → 1-[(4-Methylphenyl)sulfonyl]-1H-imidazole-2-carboxaldehyde

HRID 1987389Notes

Reaction equation

HRID 1987389 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].CCN(CC)CC.[S:15](Cl)([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16]>C(Cl)Cl>[C:21]1([CH3:22])[CH:23]=[CH:24][C:18]([S:15]([N:1]2[CH:5]=[CH:4][N:3]=[C:2]2[CH:6]=[O:7])(=[O:17])=[O:16])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 249551H-imidazole-2-carbaldehyde

Product 1

HCID 189846511-[(4-Methylphenyl)sulfonyl]-1H-imidazole-2-carboxaldehydeYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-imidazolecarboxaldehyde (1.01 g, 10.51 mmol) in CH2Cl2 (25 mL) was added Et3N (2.9 mL, 21.02 mmol) and tosyl chloride (3.01 g, 15.77 mmol) and the reaction mixture was heated to reflux overnight. Then the mixture was cooled and washed with saturated NH4Cl (4×30 mL). The organic layer was dried (MgSO4), filtered, and concentrated to afford a dark brown oil. Purification by flash column chromatography on silica gel using 2% MeOH/CH2Cl2 afforded 1-(toluene-4-sulfonyl)-1H-imidazole-2-carbaldehyde as a yellow oil (1.53 g, 58%). 1H NMR (CDCl3) δ 2.45 (s, 3H), 7.31 (s, 1H), 7.49 (d, 2H, J=6.0 Hz), 7.83 (s, 1H), 8.00 (d, 2H, J=7.5 hz), 9.78 (s, 1H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. temperatureThen the mixture was cooled
  4. washwashed with saturated NH4Cl (4×30 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a dark brown oil
  9. customPurification by flash column chromatography on silica gel using 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-81288311f7134d7a94c2ac7b0ab450b1
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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