Methyl iodide → N-(4-acetyl-phenyl)-N-methyl-methanesulfonamide

HRID 10722

반응식

HRID 10722 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:15](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]([CH3:15])[S:11]([CH3:14])(=[O:12])=[O:13])=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 6328Methyl iodide2회HCID 11430Potassium CarbonateHCID 684083N-(4-acetylphenyl)methanesulfonamide

생성물 1

HCID 12994055N-(4-acetyl-phenyl)-N-methyl-methanesulfonamide수율 64.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Ex-101A: A solution of N-(4-acetyl-phenyl)-methanesulfonamide (Ex-100A, 2.0 g, 9.4 mmol) in anhydrous DMF (300 mL) was treated with potassium carbonate (2.59 g, 18.8 mmol), followed by the addition of methyl iodide (5.85 mL, 94 mmol). The reaction mixture refluxed for two hours and was then treated with more methyl iodide (5.85 mL, 94 mmol). The reaction refluxed for another two hours, and reaction completeness was confirmed by HPLC analysis. The reaction was quenched with water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic phase was collected, dried over sodium sulfate, and concentrated to a clear oil with residual DMF. Water (25 mL) was added to precipitate a white solid. The white solid was then filtered and dried by vacuum oven at 20° C. (−20 mm Hg) to give 1.37 g (64%) of N-(4-acetyl-phenyl)-N-methyl-methanesulfonamide. 1H-NMR (CDCl3) δ 7.88 (d, 2H), 7.48 (d, 2H), 3.38 (s, 3H), 2.86 (s, 3H), 2.60 (s, 3H). HRMS m/z: calc. 530.1307, found 530.1313.

후처리

  1. temperatureThe reaction mixture refluxed for two hours
  2. temperatureThe reaction refluxed for another two hours
  3. customreaction completeness
  4. customThe reaction was quenched with water (100 mL)
  5. extractionextracted with ethyl acetate (2×100 mL)
  6. customThe organic phase was collected
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to a clear oil with residual DMF
  9. additionWater (25 mL) was added
  10. customto precipitate a white solid
  11. filtrationThe white solid was then filtered
  12. customdried by vacuum oven at 20° C. (−20 mm Hg)

출처 및 근거

ORD 기록
ord-5821600eb019413e80b830f69e75ec23
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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