Hydrochloric Acid → 3-(1-Benzylimidazol-2-yl)propionic acid hydrochloride
Reaction equation
[C:1]([O:9]CC)(=[O:8])[CH2:2][C:3](OCC)=O.[O-]CC.[Na+].Cl.[CH2:17]([N:24]1[CH:28]=[CH:27][N:26]=[C:25]1C[Cl:30])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>C(O)C>[ClH:30].[CH2:17]([N:24]1[CH:28]=[CH:27][N:26]=[C:25]1[CH2:3][CH2:2][C:1]([OH:9])=[O:8])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1Participants
Procedure
A solution of diethyl malonate (57.8 g) in absolute ethanol (100 ml) was added to a stirred solution of sodium ethoxide in absolute ethanol (prepared from sodium (8.31 g) and absolute ethanol (150 ml)). The mixture was stirred at ambient temperature for 30 minutes. The mixture was cooled in ice water and a solution of 1-benzyl-2-chloromethylimidazole hydrochloride (25.0 g) in absolute ethanol (210 ml) was added over 30 minutes. The mixture was stirred at ambient temperature for 2 hours and then concentrated under reduced pressure. Ice cold 2 M hydrochloric acid (200 ml) was added to the residue and the solution washed with ethyl acetate. The aqueous layer was neutralised with sodium carbonate and extracted with ether to give a residue which was warmed at 95° C. for 18 hours with concentrated hydrochloric acid (100 ml). The mixture was evaporated to dryness to give 3-(1-benzylimidazol-2-yl)propionic acid hydrochloride as a glasslike product.
Workup
- stirringThe mixture was stirred at ambient temperature for 2 hours
- concentrationconcentrated under reduced pressure
- additionIce cold 2 M hydrochloric acid (200 ml) was added to the residue
- washthe solution washed with ethyl acetate
- extractionextracted with ether
- customto give a residue which
- customThe mixture was evaporated to dryness
Sources & evidence
- ORD record
- ord-47d6fe0c882f47ec9ecee96920e936fd
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06326500B1
Reaction notes
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