Acetic Acid → 6-Benzenesulfonylcarbamoyl-1-(biphenyl-4-ylmethyl)-2-methoxybenzimidazole

HRID 1699621Notes

Reaction equation

CO[C:3]([O:8][CH3:9])(OC)OC.C(O)(=O)C.[C:14]1([S:20]([NH:23][C:24](=[O:46])[C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[C:27]([NH:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:36][CH:35]=3)[CH:26]=2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO>[C:14]1([S:20]([NH:23][C:24]([C:25]2[CH:30]=[CH:29][C:28]3[N:31]=[C:3]([O:8][CH3:9])[N:32]([CH2:33][C:34]4[CH:39]=[CH:38][C:37]([C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=5)=[CH:36][CH:35]=4)[C:27]=3[CH:26]=2)=[O:46])(=[O:22])=[O:21])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Tetramethoxymethane (0.250 g) is added to an acetic acid solution (3 ml) of N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino)benzamide (0.400 g), and the solution is stirred for two hours at 80° C. Methanol is added to the reaction solution, and precipitated crystals are collected. The crystals are washed in a mixture solvent of acetone (1 ml) and methanol (8 ml), separated through filtration, dried and thus, 6-benzenesulfonylcarbamoyl-1-(biphenyl-4-ylmethyl)-2-methoxybenzimidazole (0.280 g) is obtained. 1H-NMR (DMSO-d6, δ): 4.17 (3H, s), 5.33 (2H, s), 7.30 (2H, d, J=8.2 Hz), 7.35 (1H, t, J=7.4 Hz), 7.44 (2H, t, J=7.5 Hz), 7.50 (1H, d, J=8.4 Hz), 7.60-7.65 (6H, m), 7.68-7.72 (2H, m), 7.98-8.01 (2H, m), 8.05 (1H, d, J=1.5 Hz), 8.18 (1H, s), 12.50 (1H, s).

Workup

customprecipitated crystals
customare collected
washThe crystals are washed in a mixture solvent of acetone (1 ml) and methanol (8 ml)
customseparated through filtration
customdried

Sources & evidence

ORD record: ord-4fc001d619c544e1a3306b0e03e2ad56
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06348032B1

Reaction notes

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