Methanesulfonyl chloride → Methanesulfonamide, N-[2-iodo-4-(trifluoromethyl)phenyl]-

HRID 1171463ノート

反応式

HRID 1171463 の反応式
[I:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH2:12].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[I:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][S:14]([CH3:13])(=[O:16])=[O:15]

参加物

5

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 27833222-Iodo-4-(trifluoromethyl)aniline

生成物 1

HCID 21075164Methanesulfonamide, N-[2-iodo-4-(trifluoromethyl)phenyl]-収率 32.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

反応条件

温度
105 °C

実験手順

A mixture of 2-iodo-4-(trifluoromethyl)benzenamine (11.0 g, 0.0382 mol), pyridine (40 ml), methanesulfonylchloride (5.3 g, 0.046 mol) and DMAP (0.46 g, 0.0038 mol) in a 100 ml RB flask was heated slowly to 105° C. and maintained the same temperature for over night. The reaction mixture was concentrated to remove the pyridine. The crude product obtained was purified by column chromatography using 10% ethyl acetate in pet ether as eluent to get N-(2-iodo-4-(trifluoromethyl)phenyl)methanesulfonamide (4.5 g, 32%) as white solid. 1H NMR (400 MHz, CDCl3) δ 3.08 (s, 3H), 6.88 (bs, 1H), 7.65 (d, 1H), 7.75 (d, 1H), 8.07 (s, 1H).

後処理

  1. temperaturemaintained the same temperature for over night
  2. concentrationThe reaction mixture was concentrated
  3. customto remove the pyridine
  4. customThe crude product obtained
  5. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-c136f2dc6bfb4c35bc68c185cd013f30
出典データセット
uspto-grants-2010_11
特許番号
US07829571B2

反応ノート

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