Hydrochloric Acid → HCID 178482989, compound

HRID 2194670Notes

Reaction equation

HRID 2194670 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([CH:12]=O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][NH2:15].CO.[BH4-].[Na+].[ClH:20]>C(O)C>[ClH:20].[ClH:20].[CH3:14][NH:15][CH2:12][C:10]1[N:11]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 178519858HCID 178519858, compound

Product 1

HCID 178482989HCID 178482989, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 2-phenyl-1H-imidazole-4-carbaldehyde (1.73 g) in ethanol (30 mL) was added 40% methylamine-methanol solution (2.36 g) and the mixture was stirred at 65° C. for 1 hr. The mixture was allowed to cool to room temperature, sodium borohydride (571 mg) was added and the mixture was stirred for 30 min. 1 mol/L Hydrochloric acid was added to the reaction mixture, and the mixture was concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with tetrahydrofuran. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: ethyl acetate-methanol=1:0→4:1) and dissolved in methanol (10 mL). A 4 mol/L hydrogen chloride-ethyl acetate solution (5 mL) was added, and the mixture was concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound as colorless crystals (yield 1.06 g, yield 41%).

Workup

  1. temperatureto cool to room temperature
  2. stirringthe mixture was stirred for 30 min
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionA saturated aqueous sodium hydrogen carbonate solution was added to the residue
  5. extractionthe mixture was extracted with tetrahydrofuran
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by basic silica gel column chromatography (eluent: ethyl acetate-methanol=1:0→4:1)
  9. dissolutiondissolved in methanol (10 mL)
  10. additionA 4 mol/L hydrogen chloride-ethyl acetate solution (5 mL) was added
  11. concentrationthe mixture was concentrated under reduced pressure
  12. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-61bd1fd5acd3405fa61113cb47a65598
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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