Hydrochloric Acid → 1H-Imidazole, 2-(2-benzofuranyl)-, monohydrochloride

HRID 1707661Notes

Reaction equation

HRID 1707661 reaction equation
CO[CH:3](OC)[CH2:4][NH2:5].[ClH:8].[O:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=[C:10]1[C:18](=[NH:21])OC.Cl>CO.C(OCC)C.C(O)C>[ClH:8].[O:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=[C:10]1[C:18]1[NH:21][CH:3]=[CH:4][N:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 89728Aminoacetaldehyde dimethyl acetalHCID 18962029HCID 18962029, compound

Product 1

HCID 30735951H-Imidazole, 2-(2-benzofuranyl)-, monohydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21585056Diethyl ether ethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of aminoacetaldehyde dimethylacetal (7.3 g) and methyl benzofuran-2carboximidate hydrochloride (13.4 g) in methanol (135 ml) was stirred at 60° C. for 16 hours. The mixture was then evaporated to dryness. Hydrochloric acid (750 ml, 2M) was added and the resulting mixture was stirred at 60° C. for 16 hours. After cooling, the solution was washed with dichloromethane. The aqueous layer was basified with sodium hydroxide and the free base was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried. Evaporation of the solvent gave a solid residue which was dissolved in diethyl ether/ethanol. Ethereal HCl was added to solution and the precipitated salt was collected by filtration (12.5 g, 90%).

Workup

  1. customThe mixture was then evaporated to dryness
  2. additionHydrochloric acid (750 ml, 2M) was added
  3. temperatureAfter cooling
  4. washthe solution was washed with dichloromethane
  5. extractionthe free base was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. customdried
  8. customEvaporation of the solvent
  9. customgave a solid residue which
  10. filtrationthe precipitated salt was collected by filtration (12.5 g, 90%)

Sources & evidence

ORD record
ord-b9b2d16cdf8842dda987273904239159
Source dataset
uspto-grants-1994_10
Patent number
US05354769

Reaction notes

Loading…