4-Toluenesulfonyl chloride → N-(4-Bromo-benzyl)-N-(2,2-dimethoxy-ethyl)-4-methyl-benzenesulfonamide

HRID 404715노트

반응식

HRID 404715 반응식
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][NH:7][CH2:8][CH:9]([O:12][CH3:13])[O:10][CH3:11])=[CH:4][CH:3]=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>ClCCl.N1C=CC=CC=1.ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:8][CH:9]([O:10][CH3:11])[O:12][CH3:13])[S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])=[CH:14][CH:15]=1

참가 물질

5

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 59226241N-(4-Bromobenzyl)-2,2-dimethoxyethanamine

생성물 1

HCID 59226245N-(4-Bromo-benzyl)-N-(2,2-dimethoxy-ethyl)-4-methyl-benzenesulfonamide수율 63.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21875418Pyridine methylene chloride용매

실험 절차

60.5 g (4-Bromo-benzyl)-(2,2-dimethoxy-ethyl)-amine (1, crude product) were dissolved in 270 ml of dichloromethane/pyridine (8:1). At 0° C. a solution of 76.0 g (386.4 mmol) p-toluenesulfonylchloride in 100 ml of dichloromethane was added and the solution was stirred at room temperature. After 3 h, the reaction mixture was washed twice with 2 N HCl and saturated sodium hydrogen carbonate-solution. The organic layer was dried over magnesium sulfate and evaporated. Final silica gel chromatography (heptane/ethylacetate 4:1) gave 59.9 g of the title compound. Rt=1.82 min (Method C). Detected mass: 396.1/398.1 (M−OMe−).

후처리

  1. washthe reaction mixture was washed twice with 2 N HCl and saturated sodium hydrogen carbonate-solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated

출처 및 근거

ORD 기록
ord-29886b4c7422484ea3dc83b0874094f9
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748614B2

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