Acetonitrile → 1-(phenylsulfonyl)-4-formyl-1H-imidazole

HRID 922706Notes

Reaction equation

HRID 922706 reaction equation
[CH:1]([C:3]1[N:4]=[CH:5][NH:6][CH:7]=1)=[O:2].C(#N)C.C(N(CC)CC)C.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1.O>[C:18]1([S:24]([N:6]2[CH:7]=[C:3]([CH:1]=[O:2])[N:4]=[CH:5]2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 764281H-Imidazole-4-carbaldehyde

Product 1

HCID 867153981-(phenylsulfonyl)-4-formyl-1H-imidazoleYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Formylimidazole (11.7 g, 121.8 mmol) and acetonitrile (59 mL) were charged, and triethylamine (13.6 g, 133.9 mml) was added thereto at 30° C. or below. And then, a solution of benzenesulfonyl chloride (23.7 g, 133.9 mmol) in THF (35 mL) was added dropwise thereto at 30° C. or below, and the mixture was stirred at room temperature for 1 hr or more. After the reaction, water (94 mL) was added dropwise thereto at 30° C. or below for crystallization, and the mixture was stirred at room temperature for 1 hr or more, cooled to 10° C. or below, and stirred for 1 hr or more. The obtained crystals were collected by filtration, and washed with a mixed solvent (35 mL) of acetonitrile/water (1:2, volume ratio). The obtained wet crystals were dried under reduced pressure at an outside temperature of 50° C. to give 1-(phenylsulfonyl)-4-formyl-1H-imidazole (20.0 g, 84.7 mmol). yield 70%.

Workup

  1. customat 30° C. or below
  2. additionwas added dropwise
  3. customat 30° C. or below for crystallization
  4. stirringthe mixture was stirred at room temperature for 1 hr or more
  5. temperaturecooled to 10° C. or below
  6. stirringstirred for 1 hr or more
  7. filtrationThe obtained crystals were collected by filtration
  8. washwashed with a mixed solvent (35 mL) of acetonitrile/water (1:2, volume ratio)
  9. customThe obtained wet crystals were dried under reduced pressure at an outside temperature of 50° C.

Sources & evidence

ORD record
ord-6499b247debb45dfa87c938a20b4cc35
Source dataset
uspto-grants-2016_03
Patent number
US09278938B2

Reaction notes

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