Hydrogen chloride-ethyl acetate → HCID 86704968, compound

HRID 572157Notes

Reaction equation

HRID 572157 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:10]3[CH:33]=[CH:32][C:13]([O:14][C:15]4[N:19](COCC[Si](C)(C)C)[C:18]5[CH:28]=[CH:29][CH:30]=[CH:31][C:17]=5[N:16]=4)=[CH:12][CH:11]=3)[C:5]=12.C(OCC)(=O)C.Cl>CO>[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:10]3[CH:33]=[CH:32][C:13]([O:14][C:15]4[NH:19][C:18]5[CH:28]=[CH:29][CH:30]=[CH:31][C:17]=5[N:16]=4)=[CH:12][CH:11]=3)[C:5]=12

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86704967HCID 86704967, compound

Product 1

HCID 86704968HCID 86704968, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-[4-(imidazo[1,2-a]pyridin-8-yl)phenoxy]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazole (0.53 g), 4 M hydrogen chloride-ethyl acetate solution (20 ml) and methanol (4 ml) was heated under reflux for 3 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound (0.29 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3805f97388c8497896242f5b33aff36f
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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