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

HRID 2402312

反応式

HRID 2402312 の反応式
[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]

参加物

5

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 1856942-Fluoro-4-iodoaniline

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f490f36745af4f2a9b39ccdfae92449f
出典データセット
uspto-grants-2014_08
特許番号
US08796328B2

関連ノート

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