Pyridine → N-(2,2-Dimethoxy-ethyl)-N-(4-fluoro-benzyl)-4-methyl-benzenesulfonamide
Reaction equation
[CH3:1][O:2][CH:3]([O:14][CH3:15])[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.N1C=CC=CC=1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>ClCCl>[CH3:1][O:2][CH:3]([O:14][CH3:15])[CH2:4][N:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=1)[S:28]([C:25]1[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=1)(=[O:30])=[O:29]Participants
5
Procedure
20 g (2,2-Dimethoxy-ethyl)-(4-fluoro-benzyl)-amine (3) were dissolved in 120 ml of dichloromethane. 20 ml of pyridine were added. At 0° C. a solution of 23.8 g p-toluene sulfonic acid chloride in dichloromethane was added dropwise. The reaction was allowed to warm to room temperature and stirring was continued until conversion was completed. For workup, the reaction mixture was extracted twice with 2M hydrochloric acid, twice with sodium bicarbonate and once with brine. The organic layer was dried over magnesium sulfate, evaporated to dryness and the obtained crude product was purified by silica gel chromatography to yield 22.95 g of 4 as an orange oil. Rt=1.71 min (Method #4). Detected mass: 336.1 (M−OMe−).
Workup
- extractionFor workup, the reaction mixture was extracted twice with 2M hydrochloric acid, twice with sodium bicarbonate and once with brine
- dry with materialThe organic layer was dried over magnesium sulfate
- customevaporated to dryness
- customthe obtained crude product
- customwas purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-00c987a8bfd5493297bcaf5ce406576b
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710228B2
Reaction notes
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