Dichloromethane → N-[1-(2',5'-Difluoro-1,1'-biphenyl-2-yl)ethyl]-4-methoxybenzenesulfonamide

HRID 2181901

반응식

HRID 2181901 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]([NH2:29])[CH3:28].C(N(CC)CC)C.ClCCl>C(#N)C>[F:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]([NH:29][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[CH3:28]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 224822831-(2',5'-Difluoro-1,1'-biphenyl-2-yl)ethylamine

생성물 1

HCID 22482355N-[1-(2',5'-Difluoro-1,1'-biphenyl-2-yl)ethyl]-4-methoxybenzenesulfonamide수율 89.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

4-Methoxybenzenesulfonyl chloride (326 mg, 1.6 mmol) was added to a solution of 1-(2′,5′-difluoro-1,1′-biphenyl-2-yl)ethylamine (350 mg, 1.5 mmol) and triethylamine (418 uL, 3 mmol) in acetonitrile. The reaction was stirred at ambient temperature for 16 hours, whereupon dichloromethane was added and the reaction washed with water. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, and purified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g), eluting with a gradient of 30%-50% methyl tert-butyl ether in hexane (35 min), to afford the product (540 mg, 89%) as a white solid, m.p. 143-144° C.;

후처리

  1. additionwas added
  2. washthe reaction washed with water
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g)
  7. washeluting with a gradient of 30%-50% methyl tert-butyl ether in hexane (35 min)

출처 및 근거

ORD 기록
ord-23fe10fb33824342a3a5d79a7c3e8838
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894061B2

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