N,N-Dimethyl-1H-imidazole-1-sulfonamide → HCID 23510467, compound
Reaction equation
[CH3:1][N:2]([CH3:11])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)(=[O:5])=[O:4].[Li]CCCC.C1(C)C=CC=C[C:18]=1[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1>C1COCC1>[OH:28][CH:27]([C:26]1[CH:29]=[CH:30][C:23]([CH3:18])=[CH:24][CH:25]=1)[C:7]1[N:6]([S:3]([N:2]([CH3:11])[CH3:1])(=[O:4])=[O:5])[CH:10]=[CH:9][N:8]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A suspension of N,N-dimethyl-1H-imidazole-1-sulfonamide (2.02 g) in THF (50 mL) was cooled to −78° C., and thereto was added dropwise n-BuLi (4.77 mL, 2.66 M hexane solution), and the mixture was stirred for 30 minutes. To the mixture was added p-tolyl benzaldehyde (2.08 g), and the mixture was warmed to room temperature over a period of 1 hour, and then stirred for 16 hours. The mixture was extracted with aqueous hydrochloric acid solution, washed with Et2O, and basified with an aqueous NaOH solution. This solution was extracted with Et2O, and the organic layer was dried and filtered. The solvent was evaporated under reduced pressure to give 2-[hydroxy(4-methylphenyl)methyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide.
Workup
- temperaturethe mixture was warmed to room temperature over a period of 1 hour
- stirringstirred for 16 hours
- extractionThe mixture was extracted with aqueous hydrochloric acid solution
- washwashed with Et2O
- extractionThis solution was extracted with Et2O
- customthe organic layer was dried
- filtrationfiltered
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-8f0cad57b2bc4efd9f8c372b40be3cff
- Source dataset
- uspto-grants-2004_07
- Patent number
- US06759429B2
Reaction notes
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