Water → N-(5-bromo-2-chloropyridin-3-yl)-N-methylmethanesulfonamide

HRID 241050ノート

反応式

HRID 241050 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])[C:5]([Cl:8])=[N:6][CH:7]=1.[C:14](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:9]([CH3:14])[S:10]([CH3:13])(=[O:12])=[O:11])[C:5]([Cl:8])=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59519513N-(5-bromo-2-chloro-3-pyridinyl)methanesulfonamide

生成物 1

HCID 86647824N-(5-bromo-2-chloropyridin-3-yl)-N-methylmethanesulfonamide収率 90%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of N-(5-bromo-2-chloropyridin-3-yl)methanesulfonamide (96 mg, 0.34 mmol, reagent preparation 24) in DMF (1 mL) was treated with potassium carbonate (93 mg, 0.68 mmol) and iodomethane (33 uL, 0.51 mmol) at rt for 18 h. Water was then added, and the resulting aqueous mixture was extracted twice with ethyl acetate. The combined organic extracts were washed with aqueous lithium chloride (10%) followed by water, dried over magnesium sulfate, filtered, and concentrated in vacuo to provide N-(5-bromo-2-chloropyridin-3-yl)-N-methylmethanesulfonamide (91.2 mg, 0.304 mmol, 90% yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.46 (d, 1H), 8.00 (d, 1H), 3.32 (s, 3H), 3.07 (s, 3H); MS (EI) for C7H8BrClN2O2S: 299, 301, 303 (Br+Cl isotopes, MH+).

後処理

  1. extractionthe resulting aqueous mixture was extracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with aqueous lithium chloride (10%)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ae72cbfbfd894e9386653e91f9bb230c
出典データセット
uspto-grants-2014_02
特許番号
US08648066B2

反応ノート

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