4-Hydroxy-N,N,2-trimethyl-1-((4-methylphenyl)sulfonyl)-1H-benzimidazole-6-carboxamide → 5-[(Dimethylamino)methyl]-4-hydroxy-N,N,2-trimethyl-1-[(4-methylphenyl)sulfonyl]-1H-benzimidazole-6-carboxamide
Reaction equation
[OH:1][C:2]1[C:10]2[N:9]=[C:8]([CH3:11])[N:7]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[CH:5]=[C:4]([C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[CH:3]=1>ClCCl>[CH3:22][N:24]([CH2:26][C:3]1[C:4]([C:22]([N:24]([CH3:26])[CH3:25])=[O:23])=[CH:5][C:6]2[N:7]([S:12]([C:15]3[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=3)(=[O:14])=[O:13])[C:8]([CH3:11])=[N:9][C:10]=2[C:2]=1[OH:1])[CH3:25]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution of 4-hydroxy-N,N,2-trimethyl-1-[(4-methylphenyl)sulfonyl]-1H-benzimidazole-6-carboxamide (1.00 g, 2.68 mmol, Step 4) in dichloromethane (50 mL) was added N,N-dimethylmethyleneiminium iodide (545 mg, 2.95 mmol) at room temperature and the mixture was stirred at 40° C. for 15 hours. The reaction was quenched by saturated sodium hydrogencarbonate aqueous solution. The mixture was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford the title compound as a yellow amorphous (1.04 g, 90%).