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

HRID 1930196노트

반응식

HRID 1930196 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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 is 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 compound 2 as an orange oil. Rt=1.71 min (Method C). Detected mass: 336.1 (M-OMe−).

후처리

  1. extractionFor workup, the reaction mixture was extracted twice with 2M hydrochloric acid, twice with sodium bicarbonate 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

출처 및 근거

ORD 기록
ord-63c4a96aaddd40d981cf4c4ecad67754
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188117B2

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