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

HRID 1784217Notes

Reaction equation

HRID 1784217 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-c4ce1ab8900c4a21ace0be056038e3b9
Source dataset
uspto-grants-2009_03
Patent number
US07501518B2

Reaction notes

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