Benzimidazole → 1-(3-Bromo-1-propyl)benzimidazole

HRID 50996노트

반응식

HRID 50996 반응식
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[H-].[Na+].[Br:12][CH2:13][CH2:14][CH2:15]Br>CN(C=O)C>[Br:12][CH2:13][CH2:14][CH2:15][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

참가 물질

5

반응물 3

HCID 5798BenzimidazoleHCID 80011,3-DibromopropaneHCID 24758Sodium hydride

생성물 1

HCID 222523291-(3-Bromo-1-propyl)benzimidazole수율 74%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of benzimidazol (355 mg, 3.00 mmol) in dry DMF (10 mL) was added NaH (83 mg, 3.3 mmol) at 20° C. under N2 atmosphere. The reaction mixture was stirred for 30 min, and then 1,3-dibromopropane (1.82 g, 9.00 mmol) was added and stirres for additional 15 h at 20° C. The reaction was quenched by addition of H2O, and the product was extracted with EtOAc. The organic solution was then washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. 1-(3-Bromo-1-propyl)benzimidazole (530 mg, 74%) was isolated by flash chromatography on a silica gel column by elution with EtOAc/Hexanes a pale yellow oil. 1H NMR (CDCl3, 300 MHz) δ2.40 (qu, 2H, J=6.6 Hz), 3.33 (t, 2H, J=6.2 Hz), 4.42 (t, 2H, J=6.6 Hz), 7.12-7.20 (m, 1H), 7.27-7.48 (m, 2H), 7.43-7.49 (m, 1H), 7.78-7.86 (m, 1H) ppm.

후처리

  1. waitstirres for additional 15 h at 20° C
  2. customThe reaction was quenched by addition of H2O
  3. extractionthe product was extracted with EtOAc
  4. washThe organic solution was then washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-898edd5d828f4588b33757d596d816f7
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713471B1

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