N-bromobutanimide → N-benzyl-5-bromo-3-methylfuran-2-carboxamide

HRID 1887253노트

반응식

HRID 1887253 반응식
[CH2:1]([NH:8][C:9]([C:11]1[O:12][CH:13]=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>C(#N)C>[CH2:1]([NH:8][C:9]([C:11]1[O:12][C:13]([Br:17])=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 878870N-benzyl-3-methylfuran-2-carboxamide

생성물 1

HCID 47242031N-benzyl-5-bromo-3-methylfuran-2-carboxamide수율 11.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of N-benzyl-3-methylfuran-2-carboxamide (1.18 g, 5.49 mmol) in acetonitrile (25 mL) was added N-bromosuccinimide (0.98 g, 5.49 mmol). The reaction mixture was stirred for 16 hours, and then partitioned between ethyl acetate (100 mL) and water (75 mL). The organic layer was washed with 1 N sodium hydroxide solution (50 mL) and brine (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with 0-20% ethyl acetate in hexanes to afford N-benzyl-5-bromo-3-methylfuran-2-carboxamide as a colorless solid (0.18 g, 11%): 1H NMR (300 MHz, CDCl3) δ 7.38-7.27 (m, 5H), 6.54 (br s, 1H), 6.28 (s, 1H), 4.58 (d, J=5.9 Hz, 2H), 2.40 (s, 3H); MS (ES+) m/z 294.1 (M+1), 296.1 (M+1).

후처리

  1. custompartitioned between ethyl acetate (100 mL) and water (75 mL)
  2. washThe organic layer was washed with 1 N sodium hydroxide solution (50 mL) and brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluted with 0-20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-f011221204c344b2803f0549f8c5db3c
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501746B2

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