1,5-Dibromopentane → 1-(5-Bromo-pentyl)-2-methyl-4,5-diphenyl-1H-imidazole

HRID 1351012노트

반응식

HRID 1351012 반응식
[CH3:1][C:2]1[NH:3][C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.[H-].[Na+]>CN(C=O)C>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:6]1[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=[C:2]1[CH3:1]

참가 물질

5

반응물 3

HCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 2366964,5-Diphenyl-2-methylimidazole

생성물 1

HCID 185375251-(5-Bromo-pentyl)-2-methyl-4,5-diphenyl-1H-imidazole수율 67.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(Scheme 2 (E)) To a solution of 2-Methyl-4,5-diphenyl-1H-imidazole (2.0 g, 8.5 mmol) and 1,5-dibromopentane (3.01 g, 12.7 mmol) in DMF (100 mL) was added NaH (60% in mineral oil, 0.50 g, 12.7 mmol). The resulting mixture was stirred at rt for 1 hour, quenched by addition of water, extracted by CH2Cl2, washed by water, and then was dried over MgSO4. After filtration and concentration in vacuo, the residue was purified by flash chromatography (SiO2: EtOAc/Hexanes). This compound was obtained as a pale yellow oil (2.2 g, 5.7 mmol, 67% yield): 1H NMR (DMSO): δ1.20 (m, 2H), 1.47 (m, 2H), 1.64 (m, 2H), 2.41 (s, 3H), 3.45 (t, 2H), 3.72 (t, 2H), 7.16 (m, 3H), 7.31 (m, 4H), 7.55 (t, 3H). Mass Spec: 384.57 (MH+).

후처리

  1. customquenched by addition of water
  2. extractionextracted by CH2Cl2
  3. washwashed by water
  4. dry with materialwas dried over MgSO4
  5. filtrationAfter filtration and concentration in vacuo
  6. customthe residue was purified by flash chromatography (SiO2: EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-cf392448696a4f54980430c1d06b376f
출처 데이터셋
uspto-grants-2007_05
특허 번호
USRE039634E1

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