4-Aminophenol → 4-(1-methyl-4-phenyl-1H-imidazol-2-ylamino)phenol
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[C:10]1[N:11]([CH3:21])[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:14]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:21][N:11]1[CH:12]=[C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:14]=[C:10]1[NH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 120 °C
Procedure
A slurry of 4-aminophenol (0.227 g, 2.08 mmol), 2-chloro-1-methyl-4-phenyl-1H-imidazole (0.400 g, 2.08 mmol), and p-toluenesulfonic acid monohydrate (0.395 g, 2.08 mmol) was heated in 2.5 mL 2-BuOH in a sealed tube to about 110° C. for 24 h. The temperature was increased to about 120° C. and the solution was heated for 24 h. The reaction was cooled and partitioned between 50 mL pH7 buffer and DCM. The aqueous layer was extracted with DCM (3×), and the combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting brown oil was purified by silica gel chromatography (0-100% 90/10 DCM/MeOH in DCM) to give 4-(1-methyl-4-phenyl-1H-imidazol-2-ylamino)phenol as a tan solid. MS m/z=266 [M+H]+. Calc'd for C16H15N3O: 265.3.
Workup
- temperaturethe solution was heated for 24 h
- temperatureThe reaction was cooled
- custompartitioned between 50 mL pH7 buffer
- extractionThe aqueous layer was extracted with DCM (3×)
- dry with materialthe combined organics were dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resulting brown oil was purified by silica gel chromatography (0-100% 90/10 DCM/MeOH in DCM)
Sources & evidence
- ORD record
- ord-d027b8d8f70e402b87a4e4136de31d3d
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07868177B2
Reaction notes
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