4-Toluenesulfonyl chloride → 1-[(4-Methylphenyl)sulfonyl]-1H-imidazole-4-carboxaldehyde
Reaction equation
[CH:1]([C:3]1[N:4]=[CH:5][NH:6][CH:7]=1)=[O:2].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.C(N(CC)CC)C.CCCCCCC>CN(C)C(=O)C.O>[S:14]([N:6]1[CH:7]=[C:3]([CH:1]=[O:2])[N:4]=[CH:5]1)([C:11]1[CH:12]=[CH:13][C:8]([CH3:18])=[CH:9][CH:10]=1)(=[O:16])=[O:15]Participants
Procedure
4-Formylimidazole (20.0 g, 208.14 mmol) and p-toluenesulfonyl chloride (43.7 g, 229.0 mmol) were suspended in N,N-dimethylacetamide (200 mL). To the obtained suspension was added dropwise triethylamine (23.2 g, 229.0 mmol) at 10° C. or below, and the mixture was stirred at 10° C. or below for 1 hr or more. To the reaction mixture was added n-heptane (60 mL) at 30° C. or below. To the obtained solution was added dropwise water (240 mL) at 30° C. or below for crystallization. The mixture was stirred at room temperature for 1 hr or more to give crystals. The obtained crystals were collected by filtration, and washed with water (300 mL) to give wet crystals. The obtained wet crystals were dried under reduced pressure at an outside temperature of 50° C. to give 1-tosyl-4-formyl-1H-imidazole (44.2 g, 176.6 mmol). yield 85%.
Workup
- customfor crystallization
- stirringThe mixture was stirred at room temperature for 1 hr or more
- customto give crystals
- filtrationThe obtained crystals were collected by filtration
- washwashed with water (300 mL)
- customto give wet crystals
- customThe obtained wet crystals were dried under reduced pressure at an outside temperature of 50° C.
Sources & evidence
- ORD record
- ord-55cc73cf521149e091891a97668c18b0
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278938B2
Reaction notes
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