Chloromethyl Methyl Ether → HCID 21847951, compound

HRID 618728Notes

Reaction equation

HRID 618728 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[N:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:21][O:22][CH2:23]Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH2:21][O:22][CH3:23])[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 178477978HCID 178477978, compound

Product 1

HCID 21847951HCID 21847951, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(4-chlorophenyl)-4-(4-pyridyl) imidazole from Step A (200 mg, 0.78 mmol) in THF (8 mL) at room temperature was added sodium hydride (63 mg of a 60% oil dispersion, 1.57 mmol). After cooling to 0° C., methoxymethyl chloride (74 μL, 0.97 mmol) was slowly added. The reaction was stirred at 0 oC for 1 h, then at room temperature for 1 h. The reaction was quenched by the addition of 5% sodium bicarbonate solution and the mixture was extracted with ethyl acetate (2 times). The combined extracts were successively washed with 5% sodium bicarbonate solution, water and saturated salt solution and dried over anhydrous sodium sulfate. The solution was filtered and the solvent removed by rotoevaporation. The residue was purified by flash column chromatography on silica gel eluted with 0-3% methanol in methylene chloride to yield the title compound as a pale yellow solid (172 mg, 72% yield), mass spectrum (CI) m/e=300 (M+1)+.

Workup

  1. waitat room temperature for 1 h
  2. customThe reaction was quenched by the addition of 5% sodium bicarbonate solution
  3. extractionthe mixture was extracted with ethyl acetate (2 times)
  4. washThe combined extracts were successively washed with 5% sodium bicarbonate solution, water and saturated salt solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe solution was filtered
  7. customthe solvent removed by rotoevaporation
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washeluted with 0-3% methanol in methylene chloride

Sources & evidence

ORD record
ord-4f5fa9148f544efd8d91b85384dc008a
Source dataset
uspto-grants-1999_09
Patent number
US05955480

Reaction notes

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