Methyl iodide → HCID 12698958, compound

HRID 426945Notes

Reaction equation

HRID 426945 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([OH:18])[CH2:12][N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.[CH3:19]N(C)P(N(C)C)(N(C)C)=O.[H-].[Na+].IC>O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([O:18][CH3:19])[CH2:12][N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 130368alpha-2-Naphthalenyl-1H-imidazole-1-ethanol

Product 1

HCID 12698958HCID 12698958, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.38 g. of 1-[2-(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, then 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-(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
  6. waitat room temperature for 4 hours
  7. temperatureheated at 50° C. for 2 hours
  8. extractionthe resultant aqueous mixture extracted with ether
  9. washthe ether extracts washed with water
  10. dry with materialThe organic phase is dried over magnesium sulfate
  11. customevaporated
  12. customThe resulting residue may be chromatographed on silica gel
  13. custompurification of the free base
  14. washElution of the gel with 5 to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-44b3f770b8b545c7b5a17f47a76bf726
Source dataset
uspto-grants-1979_10
Patent number
US04172141

Reaction notes

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