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

HRID 1887253ノート

反応式

HRID 1887253 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f011221204c344b2803f0549f8c5db3c
出典データセット
uspto-grants-2013_08
特許番号
US08501746B2

反応ノート

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