Hydrochloric Acid → HCID 178519500, compound

HRID 618730Notes

Reaction equation

HRID 618730 reaction equation
[C:1]([C:9]1[N:10]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[N:12](COC)[C:13]=1[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[C:1]([C:9]1[N:10]=[C:11]([C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)[NH:12][C:13]=1[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21847948HCID 21847948, compound

Product 1

HCID 178519500HCID 178519500, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-benzoyl-2-(4-chlorophenyl)-1-methoxymethyl-5-(4-pyridyl)imidazole (10 mg, 0.025 mmol) in methanol (0.8 mL) containing 6 N hydrochloric acid (21 μL) at 40° C. was stirred overnight. 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 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 orange glass (4 mg, 40% yield), mass spectrum (CI) m/e=360 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-aac1ca8c24fd4ba986f5b68d4aba5ef0
Source dataset
uspto-grants-1999_09
Patent number
US05955480

Reaction notes

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