Benzoyl chloride → HCID 21847948, compound

HRID 618729Notes

Reaction equation

HRID 618729 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:19][O:20][CH3:21])[C:10]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:11][N:12]=2)=[CH:4][CH:3]=1.C([Li])CCC.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[C:27]([C:11]1[N:12]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:9]([CH2:19][O:20][CH3:21])[C:10]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 21847951HCID 21847951, compoundHCID 178418339Butyllithium

Product 1

HCID 21847948HCID 21847948, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a cooled solution of 2-(4-chlorophenyl)-1-methoxymethyl-5-(4-pyridyl)imidazole from Step B (40 mg, 0.13 mmol) in THF (0.5 mL) at -30° C. was added dropwise a solution of n-butyllithium in hexanes (93 μL of a 2.5 M solution, 0.23 mmol). The reaction was stirred at -30 to -10° C. for 90 min. After cooling to -30° C., benzoyl chloride (47 μL, 0.40 mmol) was added. The reaction was stirred overnight at room temperature. The reaction was quenched by the addition of saturated ammonium chloride solution and the mixture was extracted with ethyl acetate (2 times). The combined extracts were successively washed with 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 0-4% methanol in methylene chloride to yield the title compound as a red-brown glass (14 mg, 26% yield), mass spectrum (CI) m/e=404 (M+1)+.

Workup

  1. temperatureAfter cooling to -30° C.
  2. stirringThe reaction was stirred overnight at room temperature
  3. customThe reaction was quenched by the addition of saturated ammonium chloride solution
  4. extractionthe mixture was extracted with ethyl acetate (2 times)
  5. washThe combined extracts were successively washed with water and saturated salt solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe solution was filtered
  8. customthe solvent removed by rotoevaporation
  9. customThe residue was purified by flash column chromatography on silica gel
  10. washeluted with 0-4% methanol in methylene chloride

Sources & evidence

ORD record
ord-861418d0136e4225a40e17c57caa80e8
Source dataset
uspto-grants-1999_09
Patent number
US05955480

Reaction notes

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