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

HRID 2181901

反応式

HRID 2181901 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.;

後処理

  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)

出典と根拠

ORDレコード
ord-23fe10fb33824342a3a5d79a7c3e8838
出典データセット
uspto-grants-2005_05
特許番号
US06894061B2

関連ノート

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