Water → HCID 12698963, compound

HRID 847716Notes

Reaction equation

HRID 847716 reaction equation
[OH:1][CH:2]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[H-].[Na+].[CH3:22]I.O>CN(C)P(N(C)C)(N(C)C)=O.ClCCl.CO>[CH3:22][O:1][CH:2]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

8

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12698956HCID 12698956, compound

Product 1

HCID 12698963HCID 12698963, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 12679HexamethylphosphoramideSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 1.2 g of 1-[3-hydroxy-3-(2-naphthyl)-n-propyl]imidazole in 20 ml of dry hexamethylphosphoramide is treated between 5°-10° C. with stirring under nitrogen with 0.24 g of a 50% dispersion of sodium hydride in mineral oil. The mixture is stirred one hour at 10° C., one hour at 50° C., and then cooled in ice. Methyl iodide (0.8 g.) in 2 ml of hexamethylphosphoramide is added with stirring maintaining the temperature below 10° C. and the mixture stirred at 5° C. for 1 hour and overnight at room temperature. The resulting mixture is poured into water, the product extracted with ether and the extracts washed, dried (MgSO4) and evaporated to give a yellow oil. Chromatography on silica gel eluting with 10% methanol in dichloromethane gives pure 1-[3-methoxy-3-(2-naphthyl)-n-propyl]imidazole. This is converted to its hydrogen sulfate addition salt by dropwise addition of sulfuric acid to a solution in ether and recrystallized from methanol/ethyl acetate to give 1-[3-methoxy-3-(2-naphthyl)-n-propyl]imidazole hydrogen sulfate, m.p. 122°-122.5° C.

Workup

  1. temperaturecooled in ice
  2. stirringwith stirring
  3. temperaturemaintaining the temperature below 10° C.
  4. stirringthe mixture stirred at 5° C. for 1 hour and overnight at room temperature
  5. extractionthe product extracted with ether
  6. washthe extracts washed
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customto give a yellow oil

Sources & evidence

ORD record
ord-620d31b895cd4be6b5b28c941892528e
Source dataset
uspto-grants-1981_10
Patent number
US04293561

Reaction notes

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