Methanesulfonyl chloride → N-(2-Fluoro-4-iodophenyl)methanesulfonamide

HRID 2402312

반응식

HRID 2402312 반응식
[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:10][S:11](Cl)(=[O:13])=[O:12]>N1C=CC=CC=1.O>[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH:4][S:11]([CH3:10])(=[O:13])=[O:12]

참가 물질

5

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 1856942-Fluoro-4-iodoaniline

생성물 1

HCID 19785608N-(2-Fluoro-4-iodophenyl)methanesulfonamide수율 75.6%

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

실험 절차

To a solution of 2-fluoro-4-iodoaniline (5.0 g, 21 mmol) in pyridine (30 mL) at 0° C. was added methanesulfonyl chloride (2.5 mL, 32 mmol) dropwise. The mixture was allowed to warm to ambient temperature and stirred for 3 hours. The mixture was diluted with water and extracted three times with EtOAc. The combined organic extracts were washed with water and brine, dried over Na2SO4, and concentrated. Purification by chromatography (SiO2, 33% EtOAc/Hexanes) afforded the title compound (5.0 g, 75% yield). 1H NMR (300 MHz, DMSO-d6) δ 9.70 (s, 1H), 7.71 (dd, J=9.9, 1.9 Hz, 1H), 7.56 (ddd, J=8.4, 1.9, 1.0 Hz, 1H), 7.19 (t, J=8.4 Hz, 1H), 3.03 (s, 3H); MS (ESI; M−H) m/z 314.

후처리

  1. extractionextracted three times with EtOAc
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by chromatography (SiO2, 33% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-f490f36745af4f2a9b39ccdfae92449f
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796328B2

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