Methyl iodide → HCID 20475898, compound

HRID 905205Notes

Reaction equation

HRID 905205 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]([OH:19])[CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)[CH:6]=[CH:5]2.[CH3:20]N(C)P(N(C)C)(N(C)C)=O.[H-].[Na+].IC>O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]([O:19][CH3:20])[CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 20475913HCID 20475913, compound

Product 1

HCID 20475898HCID 20475898, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.38 g. of 1-[2-(6-methyl-2-naphthyl)-2-hydroxyethyl]imidazole in 40 ml. of hexamethylphosphoramide under nitrogen is added 480 mg. of a 56% dispersion of sodium hydride in mineral oil. After stirring for 1 hour at room temperature, the temperature is adjusted to 50° C. and stirring is continued for 1 to 2 hours. The reaction mixture is then cooled to about 5° C. and 0.74 ml. of iodomethane is added dropwise. Thereafter, the solution is stirred at 5° to 10° C. for 1 hour, at room temperature for 4 hours and then heated at 50° C. for 2 hours. The reaction mixture is then poured into water and the resultant aqueous mixture extracted with ether and the ether extracts washed with water. The organic phase is dried over magnesium sulfate and evaporated. The resulting residue may be chromatographed on silica gel to effect purification of the free base. Elution of the gel with 5 to 10% methanol in dichloromethane yields 1-[2-(6-methyl-2-naphthyl)-2-(methoxy)ethyl]imidazole.

Workup

  1. customis adjusted to 50° C.
  2. stirringstirring
  3. waitis continued for 1 to 2 hours
  4. temperatureThe reaction mixture is then cooled to about 5° C.
  5. stirringThereafter, the solution is stirred at 5° to 10° C. for 1 hour, at room temperature for 4 hours
  6. temperatureheated at 50° C. for 2 hours
  7. extractionthe resultant aqueous mixture extracted with ether
  8. washthe ether extracts washed with water
  9. dry with materialThe organic phase is dried over magnesium sulfate
  10. customevaporated
  11. customThe resulting residue may be chromatographed on silica gel
  12. custompurification of the free base
  13. washElution of the gel with 5 to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-03b1a929e8b0418cab9bd6e8faa0db0c
Source dataset
uspto-grants-1983_12
Patent number
US04423057

Reaction notes

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