Acetic Acid → (3-bromo-2-methoxy-benzyl-4,5-dihydro-1H-imidazol-2-yl)-amine
Reaction equation
C(O)(=O)C.[Br:5][C:6]1[C:7]([O:14][CH3:15])=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9][NH2:10].CS[C:18]1[N:19](C(OC)=O)[CH2:20][CH2:21][N:22]=1>CO>[Br:5][C:6]1[C:7]([O:14][CH3:15])=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9][N:10]1[CH2:21][CH2:20][N:19]=[C:18]1[NH2:22]Participants
5
Procedure
10 mL of acetic acid (HOAc) was added to a solution of 3.9 g of 3-bromo-2-methoxy-benzylamine 8 and 3.1 g of methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate in 100 mL of methanol. The resulting solution was heated to a gentle reflux and refluxed overnight. The solution was cooled to room temperature, quenched with sodium hydroxide and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over magnesium sulfate. The mixture was then filtered. The solvents were removed under vacuum. The remaining residue was purified by chromatography on silica gel (10% saturated ammonia methanol in dichloromethane) to give (3-bromo-2-methoxy-benzyl-4,5-dihydro-1H-imidazol-2-yl)-amine 9.
Workup
- temperatureThe resulting solution was heated to
- temperaturea gentle reflux
- temperaturerefluxed overnight
- customquenched with sodium hydroxide
- extractionextracted with ethyl acetate
- washThe combined organic extracts were washed with brine
- dry with materialdried over magnesium sulfate
- filtrationThe mixture was then filtered
- customThe solvents were removed under vacuum
- customThe remaining residue was purified by chromatography on silica gel (10% saturated ammonia methanol in dichloromethane)
Sources & evidence
- ORD record
- ord-d38b29436c584aff9ebd74b3f02c8b6c
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063231B2
Reaction notes
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