Hydrochloric Acid → 4-(4-Chlorophenyl)-2-(2-propyl-1-imidazolyl)-5-oxazolepropionic acid
Reaction equation
Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][C:16]([O:18]C)=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[CH2:20]([C:23]1[NH:24][CH:25]=[CH:26][N:27]=1)[CH2:21][CH3:22].[H-].[Na+].[OH-].[Na+].Cl>CN(C)C=O.O>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[N:6]=[C:2]([N:24]3[CH:25]=[CH:26][N:27]=[C:23]3[CH2:20][CH2:21][CH3:22])[O:3][C:4]=2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:12][CH:11]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
Methyl 2-chloro-4-(4-chlorophenyl)-5-oxazolepropionate (1.50 g) and 2-propylimidazole (0.66 g) were dissolved in N,N-dimethylformamide (10 ml), and sodium hydride (60% dispersion in oil, 0.30 g) was gradually added to the resulting solution at room temperature. After this was stirred at room temperature for 3.5 hours, an aqueous solution of 2 N sodium hydroxide (50 ml) was added thereto and stirred for an additional 30 minutes. Water was added to the reaction mixture, and the pH was then adjusted to 6 with 2 N hydrochloric acid. The crystals thus precipitated were collected by filtration, and recrystallized from ethanol to obtain 4-(4-chlorophenyl)-2-(2-propyl-1-imidazolyl)-5-oxazolepropionic acid (1.25 g, 69%) as pale brown needles. mp 174-175° C.
Workup
- stirringstirred for an additional 30 minutes
- customThe crystals thus precipitated
- filtrationwere collected by filtration
- customrecrystallized from ethanol
Sources & evidence
- ORD record
- ord-c8cf70e9f8dd4d50ab7f57587139c931
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06177452B1
Reaction notes
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