Pyridine → N-(2,2-Dimethoxy-ethyl)-N-(4-fluoro-benzyl)-4-methyl-benzenesulfonamide

HRID 402514ノート

反応式

HRID 402514 の反応式
[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]

参加物

5

反応物 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 11615438N-(2,2-dimethoxyethyl)-N-(4-fluorobenzyl)amine

生成物 1

HCID 59818264N-(2,2-Dimethoxy-ethyl)-N-(4-fluoro-benzyl)-4-methyl-benzenesulfonamide収率 66.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

20 g of (2,2-dimethoxy-ethyl)-(4-fluoro-benzyl)-amine (1) were dissolved in 120 ml of dichloromethane. 20 mL of pyridine were added. At 0° C. a solution of 23.8 g p-toluenesulfonic 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 washed twice with 2M hydrochloric acid, twice with sodium bicarbonate solution 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 compound 2 as an orange oil. Rt=1.71 min (Method C). Detected mass: 336.1 (M-OMe−).

後処理

  1. washFor workup, the reaction mixture was washed twice with 2M hydrochloric acid, twice with sodium bicarbonate solution and once with brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated to dryness
  4. customthe obtained crude product
  5. customwas purified by silica gel chromatography

出典と根拠

ORDレコード
ord-345775406dc84df9ba89fc3841ecb811
出典データセット
uspto-grants-2014_06
特許番号
US08742116B2

反応ノート

読み込み中…