Imidazole → HCID 21288112, compound

HRID 868271Notes

Reaction equation

HRID 868271 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:14](Br)[CH3:15])[CH:10]=2)[CH:5]=1)(=[O:3])[CH3:2].[N-:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.[Na+].[H-].[Na+].N1C=CN=C1.[I-].[K+]>CN(C)C=O>[C:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:14]([N:17]3[CH:21]=[CH:20][N:19]=[CH:18]3)[CH3:15])[CH:10]=2)[CH:5]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 795ImidazoleHCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 4605971Sodium ImidazoleHCID 13715280HCID 13715280, compound

Product 1

HCID 21288112HCID 21288112, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.82 g (35.4 mmol) of 2-acetyl-6-(1-bromoethyl)naphthalene, 6.38 g (70.9 mmol) of sodium imidazolide (from 3.1 g (70.9 mmol) of sodium hydride dispersion (55%) and 4.83 g (70.9 mmol) of imidazole) and 0.588 g (3.54 mmol) of potassium iodide in 100 ml of absolute N,N-dimethylformamide are stirred at 100° C. (24 hours). The mixture is then evaporated in vacuo, the residue is taken up in 4N HCl, the solution is extracted with ethyl acetate, and the aqueous phase is neutralized with sodium carbonate solution. It is then extracted 4× with dichloromethane, and the dichloromethane phase is dried and evaporated in vacuo. The residue is filtered through silica gel using ethyl acetate/methanol 8:1. 6.48 g (70%) of 2-acetyl-6-[1-(1-imidazolyl)ethyl]naphthalene are obtained as an oil. RF (ethyl acetate/methanol 8:1): 0.15.

Workup

  1. customThe mixture is then evaporated in vacuo
  2. extractionthe solution is extracted with ethyl acetate
  3. extractionIt is then extracted 4× with dichloromethane
  4. dry with materialthe dichloromethane phase is dried
  5. customevaporated in vacuo
  6. filtrationThe residue is filtered through silica gel

Sources & evidence

ORD record
ord-8557adce2576457294d125e16de0ea3d
Source dataset
uspto-grants-1988_10
Patent number
US04778817

Reaction notes

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