Benzyl Chloride → 2-Amino-1-benzylbenzimidazole

HRID 252200노트

반응식

HRID 252200 반응식
[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

참가 물질

5

반응물 3

HCID 7503Benzyl ChlorideHCID 136242-AminobenzimidazoleHCID 2723922Sodium ethoxide

생성물 1

HCID 1707422-Amino-1-benzylbenzimidazole수율 39%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a1bb42c2b1844d15a110df80e4d73138
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868028B2

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