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

HRID 412202Notes

Reaction equation

HRID 412202 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(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+).

Workup

  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)

Sources & evidence

ORD record
ord-1c840ee17f0d4a8d9ce21065d20eed5c
Source dataset
uspto-grants-2003_05
Patent number
US06562846B2

Reaction notes

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