Benzylamine → N-benzyl-3-methylfuran-2-carboxamide

HRID 1887249ノート

反応式

HRID 1887249 の反応式
[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([OH:9])=O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)C(C)C)(C)C.[CH2:41]([NH2:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:41]([NH:48][C:7]([C:3]1[O:4][CH:5]=[CH:6][C:2]=1[CH3:1])=[O:9])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

参加物

8

反応物 5

HCID 7504BenzylamineHCID 757711-HydroxybenzotriazoleHCID 781273-Methyl-2-furoic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 878870N-benzyl-3-methylfuran-2-carboxamide収率 80%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 3-methylfuran-2-carboxylic acid (0.79 g, 6.28 mmol), 1-hydroxybenzotriazole (1.27 g, 9.42 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.81 g, 9.42 mmol) in N,N-dimethylformamide (6 mL) was added N,N-diisopropylethylamine (3.30 mL, 18.94 mmol) and benzylamine (0.69 mL, 6.28 mmol). The reaction mixture was stirred for 16 hours, and then diluted with ethyl acetate (75 mL). The organic layer was washed with 10% aqueous hydrochloric acid (2×25 mL), saturated aqueous sodium bicarbonate (2×25 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford N-benzyl-3-methylfuran-2-carboxamide as a light brown solid (0.57 g, 80%): 1H NMR (300 MHz, CDCl3) δ 7.37-7.28 (m, 5H), 7.27 (d, J=1.5 Hz, 1H), 6.61 (br s, 1H), 6.34 (d, J=1.5 Hz, 1H), 4.59 (d, J=5.9 Hz, 2H), 2.42 (s, 3H); MS (ES+) m/z 216.2 (M+1).

後処理

  1. washThe organic layer was washed with 10% aqueous hydrochloric acid (2×25 mL), saturated aqueous sodium bicarbonate (2×25 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a27f6d3053db470ab6c0a068ba082a3f
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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