Methyl iodide → HCID 20475898, compound

HRID 1277431Notes

Reaction equation

HRID 1277431 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-01ad45c08e634cada8689b9125b1e61f
Source dataset
uspto-grants-1981_07
Patent number
US04277486

Reaction notes

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