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

HRID 623364노트

반응식

HRID 623364 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-f03b24d27e0147d8a357eb2915febbb9
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302985B2

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