Dimethylamine → 1-[3-(N,N-dimethylcarbamoyl)butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole
Reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]([CH:7]([CH3:29])[CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([CH3:19])[C:13]=2[N:12]=[C:11]1[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)=[O:6]>CO>[CH3:1][N:2]([CH3:3])[C:5]([CH:7]([CH3:29])[CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([CH3:19])[C:13]=2[N:12]=[C:11]1[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)=[O:6]Participants
4
Procedure
In an dimethylamine (40% in water, 10 ml) was placed 1-[3-(chlorocarbonyl)butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole (600 mg, 1.5 mmol). To this mixture 10 ml of methanol were added, to enhance solubility and the mixture was stirred for about 64 hours at room temperature. The reaction mixture was then concentrated under reduced pressure to produce 600 mg as a tan foam. The crude material was further purified by flash silica gel chromatography, eluting with a gradient solvent of 19:1 ethyl acetate:methanol to 9:1 ethyl acetate:methanol. The fractions containing the desired material were combined and concentrated in vacuo to yield 375 mg (63%) of the desired title compound as a white foam.
Workup
- concentrationThe reaction mixture was then concentrated under reduced pressure
- customto produce 600 mg as a tan foam
- customThe crude material was further purified by flash silica gel chromatography
- washeluting with a gradient solvent of 19:1 ethyl acetate
- additionThe fractions containing the desired material
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-ed3870bca52b4898b8501885a712ae65
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06255494B1
Reaction notes
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