Benzoyl chloride → 2-benzamido-N-benzylisonicotinamide

HRID 714313ノート

反応式

HRID 714313 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][N:17]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].CN(C1C=CC=CN=1)C.C(N(CC)C(C)C)(C)C.[C:36](Cl)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O1CCCC1.C(OCC)(=O)C>[C:36]([NH:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][N:17]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

参加物

7

反応物 4

HCID 7412Benzoyl chlorideHCID 218852-DimethylaminopyridineHCID 81531DiisopropylethylamineHCID 187528972-amino-N-benzylisonicotinamide

生成物 1

HCID 671538562-benzamido-N-benzylisonicotinamide収率 15%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-amino-N-benzylisonicotinamide (0.23 g, 0.43 mmol), dimethylaminopyridine (0.01 g, 0.08 mmol) and N,N-diisopropylethylamine (0.3 mL, 1.7 mmol) in tetrahydrofuran (10 mL) at 0° C. was added benzoyl chloride (0.12 mL, 1.00 mmol). The resulting solution was warmed to ambient temperature and stirred for 18 hours, diluted with ethyl acetate (30 mL), washed with water (20 mL) and brine (20 mL). The organic solution was dried over anhydrous sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give 2-benzamido-N-benzylisonicotinamide (0.02 g, 15%): mp 174-176° C.; 1H NMR (300 MHz, CDCl3) δ 8.86 (br s, 1H), 8.72 (s, 1H), 8.38 (d, J=5.1 Hz, 1H), 7.91-7.82 (m, 2H), 7.60-7.32 (m, 9H), 6.73 (br s, 1H), 4.64 (d, J=5.7 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ 165.9, 165.0, 151.9, 148.3, 144.4, 137.4, 133.5, 132.7, 129.0, 128.8, 128.0, 127.8, 127.2, 118.6, 110.5, 44.3; MS (ES+) m/z 332.5 (M+1).

後処理

  1. washwashed with water (20 mL) and brine (20 mL)
  2. dry with materialThe organic solution was dried over anhydrous sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-89812048d6924ea0a37829aadf0445ab
出典データセット
uspto-grants-2015_11
特許番号
US09187426B2

反応ノート

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