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

HRID 1707662Notes

Reaction equation

HRID 1707662 reaction equation
[ClH:1].[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]1[NH:12][CH:13]=[CH:14][N:15]=1.[H-].[Na+].[CH3:18]I.Cl>CN(C=O)C.C(OCC)C.C(O)C.O>[ClH:1].[CH3:18][N:15]1[CH:14]=[CH:13][N:12]=[C:11]1[C:3]1[O:2][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 30735951H-Imidazole, 2-(2-benzofuranyl)-, monohydrochloride

Product 1

HCID 30735971H-Imidazole, 2-(2-benzofuranyl)-1-methyl-, monohydrochloride

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21585056Diethyl ether ethanolSolvent

Procedure

To a solution of the free base (7.0 g) generated from 2-(benzofuran-2-yl)imidazole hydrochloride in DMF (50 ml) at 0° C. was added sodium hydride (1.4 g) 80% in mineral oil in three equal portions. After 30 minutes at room temperature, methyl iodide (2.5 ml) was added dropwise over 15 minutes at 0° C. The mixture was then stirred for 30 minutes at room temperature, poured into water and extracted with ethyl acetate. The organic layer was washed with water and the product was extracted with hydrochloric acid (1M). The aqueous layer was basified with sodium hydroxide and the free base was extracted with ethyl acetate, 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 (8.1 g, 91%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. extractionthe product was extracted with hydrochloric acid (1M)
  4. extractionthe free base was extracted with ethyl acetate
  5. washwashed with saturated brine
  6. customdried
  7. customEvaporation of the solvent
  8. customgave a solid residue which
  9. filtrationthe precipitated salt was collected by filtration (8.1 g, 91%)

Sources & evidence

ORD record
ord-19ec5445c00f4e16a0ee0c4a8f5a4475
Source dataset
uspto-grants-1994_10
Patent number
US05354769

Reaction notes

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