Water → HCID 21700499, compound

HRID 1597455Notes

Reaction equation

HRID 1597455 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:5][CH:6]=1.[H-].[Na+].[CH3:15][O:16][CH2:17]Cl.O>CN(C=O)C>[CH3:15][O:16][CH2:17][N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[C:4]1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 178430841HCID 178430841, compound

Product 1

HCID 21700499HCID 21700499, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1.0 g (6.32 mmol) of 4-methyl-2-phenylimidazole in 25 mL of DMF at 0° C. was added 278 mg (6.95 mmol, 60% in oil) of NaH. After stirring for 5 min, 0.528 mL (6.95 mmol) of chloromethyl methyl ether was added, and the reaction was warmed to 25° C. and stirred 4 h. The reaction was poured into H2O, and the product was extracted with hexanes/EtOAc (1:1). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. Purification by silica gel flash column chromatography using hexanes/EtOAc (5:95) as eluent provided 816 mg (64%) of title compound: low resolution MS (ES) m/e 225 (MNa+), 203 (MH+).

Workup

  1. stirringstirred 4 h
  2. extractionthe product was extracted with hexanes/EtOAc (1:1)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel flash column chromatography

Sources & evidence

ORD record
ord-b2474bddafe94756ab71d7834a4924c4
Source dataset
uspto-grants-2001_09
Patent number
US06294580B1

Reaction notes

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