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

HRID 241050노트

반응식

HRID 241050 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-ae72cbfbfd894e9386653e91f9bb230c
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648066B2

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