Methyl iodide → Methyl 2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinate

HRID 1436585ノート

反応式

HRID 1436585 の反応式
[H-].[Na+].[CH3:3][O:4][C:5](=[O:18])[C:6]1[CH:11]=[C:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[N:9]=[C:8]([Cl:17])[CH:7]=1.I[CH3:20]>CN(C=O)C>[CH3:3][O:4][C:5](=[O:18])[C:6]1[CH:11]=[C:10]([N:12]([S:13]([CH3:16])(=[O:14])=[O:15])[CH3:20])[N:9]=[C:8]([Cl:17])[CH:7]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86615008Methyl 2-chloro-6-methanesulphonylamino-isonicotinate

生成物 1

HCID 86612064Methyl 2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinate収率 72.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Add sodium hydride (257 mg, 6.43 mmol, 60% dispersion in mineral oil) at 0° C. to a solution of 2-chloro-6-methanesulfonylamino-isonicotinic acid methyl ester (1.31 g, 4.95 mmol) in DMF (10 mL). After stirring at 0° C. for 15 min, add iodomethane (0.4 mL, 6.43 mmol). Stir the reaction at 0° C. for 1 h and at room temperature for 2 h. Quench the reaction with ice and extract the reaction mixture with ethyl acetate. Wash the organic layer with saturated aqueous sodium chloride, dry (sodium sulfate), concentrate and purify (silica gel chromatography, eluting with 30:70 ethyl acetate:hexanes) to give the title compound (1.0 g,72%).

後処理

  1. stirringStir
  2. customthe reaction at 0° C. for 1 h
  3. waitat room temperature for 2 h
  4. customQuench
  5. customthe reaction with ice
  6. extractionextract the reaction mixture with ethyl acetate
  7. washWash the organic layer with saturated aqueous sodium chloride
  8. dry with materialdry (sodium sulfate)
  9. concentrationconcentrate
  10. custompurify
  11. wash(silica gel chromatography, eluting with 30:70 ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-9a0f7221b90145a9870c2225921b03e7
出典データセット
uspto-grants-2009_11
特許番号
US07618978B2

反応ノート

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