Methanesulfonyl chloride → N-(5-Acetyl-2-chlorophenyl)methanesulfonamide

HRID 1061211ノート

反応式

HRID 1061211 の反応式
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:17])=[C:8]([NH:10]C2C=CC=CC=2)[CH:9]=1)(=[O:3])[CH3:2].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl.N1C=CC=CC=1>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:17])=[C:8]([NH:10][S:19]([CH3:18])(=[O:21])=[O:20])[CH:9]=1)(=[O:3])[CH3:2]

参加物

5

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 69654843HCID 69654843、化合物

生成物 1

HCID 22220251N-(5-Acetyl-2-chlorophenyl)methanesulfonamide収率 57%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a stirred solution of 5-acetyl-2-chloro-phenylaniline (which was obtained in Example 22) (7.40 g, 43.5 mmol) in CH2Cl2 (200 mL) and pyridine (40 mL) at 0˜5° C. was added dropwise methanesulfonyl chloride (5.0 g, 43.6 mmol) in 50 mL of CH2Cl2. After 1 hour at 0° C. the mixture was warmed to room temperature and stirred at room temperature for another hour. The solvents were removed and the residue was dissolved in CH2Cl2(500 mL). The reaction mixture was washed with water and the organic layer was dried (MgSO4) and concentrated. The product was purified by flash silica gel chromatography eluting with ethyl acetate and hexanes to give the title compound as a white solid (6.1 g, 57%); 1H NMR (300 MHz, DMSO-d6) δ 2.58 (s, 3H), 3.08 (s, 3H), 7.69 (d, J=8.3 Hz, 1H), 7.83 (dd, J=8.3, 2.1 Hz, 1H), 7.94 (d, J=2.1 Hz, 1H), 9.69 (s, 1H); MS (ES) m/z: 245.9 ((M−H)−, 100%); HRMS Calcd. for C9H11ClNO3S(MH+): 248.0148. Found: 248.0135.

後処理

  1. customThe solvents were removed
  2. dissolutionthe residue was dissolved in CH2Cl2(500 mL)
  3. washThe reaction mixture was washed with water
  4. dry with materialthe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customThe product was purified by flash silica gel chromatography
  7. washeluting with ethyl acetate and hexanes

出典と根拠

ORDレコード
ord-e653cc6d5e734db4bd53d9ab7241b64c
出典データセット
uspto-grants-2003_02
特許番号
US06525202B2

反応ノート

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