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

HRID 1258470Notes

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

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%).

Workup

customThe reaction was quenched by saturated sodium hydrogencarbonate aqueous solution
extractionThe mixture was extracted with dichloromethane
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-94d618027daa474888184d89920ef7a1
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466166B2

Reaction notes

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