Methanol → 1-[3-(N-methylcarbamoyl)butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole
Reaction equation
C([O:3][C:4]([CH:6]([CH3:28])[CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:12]=2[N:11]=[C:10]1[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)=O)C.CO.[CH3:31][NH2:32]>>[CH3:31][NH:32][C:4]([CH:6]([CH3:28])[CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:12]=2[N:11]=[C:10]1[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)=[O:3]Participants
Procedure
In methylamine (40% in water, 20 ml), 1-[3-(ethoxycarbonyl)butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole (1.50 g, 3.7 mmol) was placed. To this mixture 10 ml of methanol were added, to enhance solubility. The resulting mixture was stirred at room temperature for about 64 hours, after which time the reaction mixture was concentrated in vacuo. The residue was taken up in 200 ml of methylene chloride. The organic fraction was washed once with 200 ml of water. The organic fraction was dried over potassium carbonate and the solvents were removed in vacuo to yield 1.61 grams of a dark oil. The crude material was further purified by flash silica gel chromatography, eluting with a gradient of methylene chlor ide to a 1:1 methylene chloride:ethyl acetate mixture. The fractions containing the desired material were combined and concentrated under reduced pressure to yield 510 mg (36%) of the desired title product as a white solid.
Workup
- concentrationafter which time the reaction mixture was concentrated in vacuo
- washThe organic fraction was washed once with 200 ml of water
- dry with materialThe organic fraction was dried over potassium carbonate
- customthe solvents were removed in vacuo
Sources & evidence
- ORD record
- ord-170bba1da86b4b93a204a244e2781633
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06255494B1
Reaction notes
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