Benzyl Chloride → 2-Amino-1-benzylbenzimidazole

HRID 252200ノート

反応式

HRID 252200 の反応式
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.CC[O-].[Na+].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCO>[NH2:1][C:2]1[N:6]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

参加物

5

反応物 3

HCID 7503Benzyl ChlorideHCID 136242-AminobenzimidazoleHCID 2723922Sodium ethoxide

生成物 1

HCID 1707422-Amino-1-benzylbenzimidazole収率 39%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 2-aminobenzimidazole (2) (Aldrich, 6 g., 45 mmol) in EtOH (10 mL) was added EtONa (21% in EtOH, 16.83 mL, 45 mmol) and benzyl chloride (5.70 mL, 50 mmol) and the brown solution was refluxed for 3 days under N2 gas. After cooling to room temperature, the reaction mixture was filtered through celite and concentrated in vacuo. The resulting brown solid was filtered hot in 300 mL acetone and crystallized from approximately 100 mL of acetone, and gave 3 as brown crystals (3.91 g., 39%). Recrystallization of the mother liquor afforded additional 3 as brown crystals (0.70 g., 7%). 1H-NMR (DMSO-d6) δ 5.27 (s, 2H), 6.61 (s, 2H), 6.82 (t, J=8.8 Hz, 1H), 6.93 (t, J=6.4 Hz, 1H), 7.05 (d, J=8.0 Hz, 1H), 7.15 (d, 7.2 Hz, 1H), 7.20 (d, 6.8 Hz, 2H), 7.24 (d, 7.6 Hz, 1H), 7.31 (t, 7.6 Hz, 2H); 13C-NMR (DMSO-d6) 45.11, 108.30, 115.19, 118.49, 120.88, 127.39, 127.66, 128.91, 134.60, 137.64, 143.34, 155.46.

後処理

  1. temperaturethe brown solution was refluxed for 3 days under N2 gas
  2. filtrationthe reaction mixture was filtered through celite and
  3. concentrationconcentrated in vacuo
  4. filtrationThe resulting brown solid was filtered hot in 300 mL acetone
  5. customcrystallized from approximately 100 mL of acetone

出典と根拠

ORDレコード
ord-a1bb42c2b1844d15a110df80e4d73138
出典データセット
uspto-grants-2011_01
特許番号
US07868028B2

反応ノート

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