Reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]([CH3:12])[C:10](=[O:13])[N:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])[C:8]=2[CH:23]=1)([OH:3])=O.[CH2:24]([S:28]([NH2:31])(=[O:30])=[O:29])[CH2:25][CH2:26][CH3:27].C1CCN2C(=NCCC2)CC1>CN(C)C=O>[CH2:24]([S:28]([NH:31][C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]([CH3:12])[C:10](=[O:13])[N:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])[C:8]=2[CH:23]=1)=[O:3])(=[O:30])=[O:29])[CH2:25][CH2:26][CH3:27]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In the same manner as in Example 1, N,N′-carbonyldiimidazole (0.290 g) was added to a mixture of 6-carboxy-1-(2,4-dichlorobenzyl)-3-methyl-2-benzimidazolone (0.314 g) and N,N-dimethylformamide (9 ml), and the mixture was stirred at room temperature for 1 hr. 1-n-Butanesulfonamide (0.246 g) and DBU (0.273 g) were added and the mixture was stirred at 100° C. for 16 hr. The solvent was evaporated and the resulting mixture was extracted with chloroform and water. The organic layer was concentrated and the residue was purified by preparative thin layer chromatography to give 6-(1-n-butanesulfonylcarbamoyl)-1-(2,4-dichlorobenzyl)-3-methyl-2-benzimidazolone (0.123 g).
Workup
- stirringthe mixture was stirred at 100° C. for 16 hr
- customThe solvent was evaporated
- extractionthe resulting mixture was extracted with chloroform and water
- concentrationThe organic layer was concentrated
- customthe residue was purified by preparative thin layer chromatography
Sources & evidence
- ORD record
- ord-8b93bcaac0704066b3b7b120e0d3fb05
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06911469B2
Linked notes
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