Imidazole → 1-[2-(2-Naphthyl)-2,2-dimethoxyethyl]imidazole

HRID 26542Notes

Reaction equation

HRID 26542 reaction equation
[OH-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[H][H].[CH3:10][O:11][C:12]([O:27][CH3:28])([C:23](CBr)=O)[C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1>CN(C)C=O.O>[CH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[C:12]([O:11][CH3:10])([O:27][CH3:28])[CH2:23][N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 14798Sodium HydroxideHCID 86736482Bromomethyl 2-naphthoyl ketone dimethyl ketalHCID 178418361HCID 178418361, compound

Product 1

HCID 126989371-[2-(2-Naphthyl)-2,2-dimethoxyethyl]imidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydroxide (0.40 g. of 50% dispersion in mineral oil) is added to 0.61 g. imidazole in 10 ml dimethylformamide and the mixture stirred at room temperature until the evolution of hydrogen is complete. Bromomethyl 2-naphthoyl ketone dimethyl ketal (2.21 g.) in 5 ml. dimethylformamide is then added and the mixture stirred for 24 hours at 110° under nitrogen. The resulting solution is poured into water (400 ml), extracted with ether (400 ml total), and the extracts washed, dried (MgSO4) and evaporated. The resulting crude solid (2.2 g) is recrystallized from toluene to give 1-[2-(2-naphthyl)-2,2-dimethoxyethyl]imidazole as a colorless solid.

Workup

  1. extractionextracted with ether (400 ml total)
  2. washthe extracts washed
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe resulting crude solid (2.2 g) is recrystallized from toluene

Sources & evidence

ORD record
ord-e17b2a24b9b4443fb29dd5a58e75c0fb
Source dataset
uspto-grants-1979_04
Patent number
US04150153

Reaction notes

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