Pyridine → 4-Bromo-N-[2-(trifluoromethyl)phenyl]benzenesulfonamide

HRID 623364ノート

反応式

HRID 623364 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].N1C=CC=CC=1.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(Cl)Cl>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=2[C:2]([F:10])([F:11])[F:1])(=[O:27])=[O:26])=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 69222-(Trifluoromethyl)anilineHCID 7396p-Bromobenzenesulfonyl chloride

生成物 1

HCID 51542164-Bromo-N-[2-(trifluoromethyl)phenyl]benzenesulfonamide収率 48.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 2-(trifluoromethyl) aniline (693 mg, 4.30 mmol) and pyridine (438 μL, 5.87 mmol) in DCM (40 mL) was treated with 4-bromobenzene sulfonyl chloride (1.0 g, 3.91 mmol) and stirred at room temperature for 18 hours. The mixture was diluted with DCM, washed with 1N HCl, sat. NaHCO3, water and brine, dried over Na2SO4 and concentrated under vacuum. Purification by silica gel column chromatography (0-20% EtOAc in cyclohexane) and triturating with pentane gave 4-bromo-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide (719 mg, 48% yield) as a colourless crystalline solid. 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=8.2 Hz, 1H), 7.65-7.47 (m, 6H), 7.29-7.20 (m, 1H), 6.85 (br s, 1H), LCMS (m/z, Method A) ES+ 380.0 [M+1]+.

後処理

  1. washwashed with 1N HCl, sat. NaHCO3, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customPurification by silica gel column chromatography (0-20% EtOAc in cyclohexane)
  5. customtriturating with pentane

出典と根拠

ORDレコード
ord-f03b24d27e0147d8a357eb2915febbb9
出典データセット
uspto-grants-2016_04
特許番号
US09302985B2

反応ノート

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