4-Toluenesulfonyl chloride → N-(4-bromo-2-iodo-5-trifluoromethyl-phenyl)-4-methyl benzynesulfonamide

HRID 513851

反応式

HRID 513851 の反応式
[Br:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([NH2:12])=[C:4]([I:13])[CH:3]=1.[C:14]1(C)[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.[OH-].[Na+].[F-].[CH2:28]([N+](CCCC)(CCCC)CCCC)CCC>N1C=CC=CC=1.C(OCC)(=O)C.O1CCCC1>[Br:1][C:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][C:5]([NH:12][S:20]([C:17]2[C:18]#[C:19][CH:14]=[CH:15][C:16]=2[CH3:28])(=[O:21])=[O:22])=[C:4]([I:13])[CH:3]=1

参加物

8

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 2724141Tetrabutylammonium FluorideHCID 455880634-Bromo-2-iodo-5-(trifluoromethyl)aniline

生成物 1

HCID 68004772N-(4-bromo-2-iodo-5-trifluoromethyl-phenyl)-4-methyl benzynesulfonamide収率 95%

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒2 回

実験手順

4-Bromo-2-iodo-5-trifluoromethyl-phenylamine (366 mg, 1.0 mmol) and p-toluene sulfonyl chloride (286 mg, 1.5 mmol, 1.5 eq.) were dissolved in anhydrous pyridine (2.5 ml). This was stirred at room temperature for 16 hours. An aqueous solution of 1 M sodium hydroxide was added to the reaction mixture, and this was stirred for five minutes. The reaction mixture was diluted with ethyl acetate. The organic layer was isolated, and washed with an aqueous solution of 1 M hydrochloric acid and an aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and concentration was performed. Then, the residue obtained by concentration under reduced pressure was dissolved in tetrahydrofuran (THF) (2.5 ml), and then a tetrahydrofuran (THF) solution of 1 M tetrabutylammonium fluoride was added thereto. This was stirred at room temperature for 17 hours. The reaction mixture was diluted with ethyl acetate. The organic layer was isolated, and washed with water and an aqueous solution saturated with sodium chloride, and then dried over anhydrous sodium sulfate. The desiccant was removed by filtration and concentration was performed. Then, the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography. Thus, N-(4-bromo-2-iodo-5-trifluoromethyl-phenyl)-4-methyl benzynesulfonamide was obtained as a pale brown solid (494 mg, three-step yield of 95%).

後処理

  1. stirringthis was stirred for five minutes
  2. customThe organic layer was isolated
  3. washwashed with an aqueous solution of 1 M hydrochloric acid
  4. dry with materialan aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate
  5. customThe desiccant was removed by filtration, and concentration
  6. customThen, the residue obtained by concentration under reduced pressure
  7. stirringThis was stirred at room temperature for 17 hours
  8. customThe organic layer was isolated
  9. washwashed with water
  10. dry with materialan aqueous solution saturated with sodium chloride, and then dried over anhydrous sodium sulfate
  11. customThe desiccant was removed by filtration and concentration
  12. customThen, the residue obtained by concentration under reduced pressure
  13. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-eabe5dc877cd45b9b928a6ac111cf0a0
出典データセット
uspto-grants-2015_08
特許番号
US09102692B2

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