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

HRID 1351012ノート

反応式

HRID 1351012 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(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+).

後処理

  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)

出典と根拠

ORDレコード
ord-cf392448696a4f54980430c1d06b376f
出典データセット
uspto-grants-2007_05
特許番号
USRE039634E1

反応ノート

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