Methyl iodide → 6-[2-(4-Bromo-2-chloro-phenyl)-propionyl]-3-methyl-3H-benzooxazol-2-one

HRID 2386821ノート

反応式

HRID 2386821 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:21]=[CH:20][C:14]3[N:15]([CH3:19])[C:16](=[O:18])[O:17][C:13]=3[CH:12]=2)=[O:10])=[C:4]([Cl:22])[CH:3]=1.[H-].[Na+].[CH3:25]I>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:25])[C:9]([C:11]2[CH:21]=[CH:20][C:14]3[N:15]([CH3:19])[C:16](=[O:18])[O:17][C:13]=3[CH:12]=2)=[O:10])=[C:4]([Cl:22])[CH:3]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 666971236-[2-(4-Bromo-2-chloro-phenyl)-acetyl]-3-methyl-3H-benzooxazol-2-one

生成物 1

HCID 666971076-[2-(4-Bromo-2-chloro-phenyl)-propionyl]-3-methyl-3H-benzooxazol-2-one収率 69%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

6-[2-(4-Bromo-2-chloro-phenyl)-acetyl]-3-methyl-3H-benzooxazol-2-one (747 mg) was dissolved in DMF (20 mL). The mixture was cooled to 0° C. To this solution was added sodium hydride (55% in mineral oil, 90 mg). The mixture was stirred for 10 minutes at 0° C. and then for 1 hour at r.t. The mixture was cooled to 0° C. and methyl iodide (292 mg) was added dropwise over a period of 10 minutes. Stirring was continued over night at r.t. The reaction mixture was poured into ice/water and extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a brown foam (531 mg, 69%). MS (neg. ion, m/e)=394.2 [(M−H)−].

後処理

  1. waitfor 1 hour at r.t
  2. temperatureThe mixture was cooled to 0° C.
  3. stirringStirring
  4. waitwas continued over night at r.t
  5. extractionextracted two times with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

出典と根拠

ORDレコード
ord-80660778f67c478a8c62c35593047f29
出典データセット
uspto-grants-2012_09
特許番号
US08268820B2

反応ノート

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