Potassium Bicarbonate → N-benzenesulfonyl-4-acetylamino-3-(4-benzyloxybenzylamino)benzamide

HRID 1699627Notes

Reaction equation

[K].[C:2]1([S:8]([NH:11][C:12](=[O:24])[C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:22])[CH3:21])=[C:15]([NH2:23])[CH:14]=2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([O:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)(O)[O-].[K+]>CN(C)C=O>[C:2]1([S:8]([NH:11][C:12](=[O:24])[C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:22])[CH3:21])=[C:15]([NH:23][CH2:37][C:36]3[CH:39]=[CH:40][C:33]([O:32][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:34][CH:35]=3)[CH:14]=2)(=[O:9])=[O:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of N-benzenesulfonyl-3-amino-4-acetylaminobenzamide potassium salt (0.500 g), 4-benzyloxybenzyl bromide (0.470 g), 20% potassium bicarbonate aqueous solution (0.925 g) and N,N-dimethylformamide (3 ml) is stirred for one hour at 90° C. The reaction solution is concentrated and purified through silica gel column chromatography (eluate: ethyl acetate/methanol=9/1) to obtain preliminarily purified N-benzenesulfonyl-4-acetylamino-3-(4-benzyloxybenzylamino)benzamide. This material underwent cyclization and thus, 6-benzenesulfonylcarbamoyl-1-(4-benzyloxybenzyl)-2-methylbenzimidazole (0.160 g) is obtained. 1H-NMR (DMSO-d6, δ): 2.54 (3H, s), 5.05 (2H, s), 5.44 (2H, s). 7.09 (2H, d, J=8.7 Hz), 7.32 (2H, d, J=7.0 Hz), 7.29-7.44 (5H, m), 7.58-7.67 (3H, m), 7.68-7.75 (2H, m), 7.79-8.02 (2H, m), 8.18 (1H, s), 12.46 (1H, s).

Workup

concentrationThe reaction solution is concentrated
custompurified through silica gel column chromatography (eluate: ethyl acetate/methanol=9/1)

Sources & evidence

ORD record: ord-9f9b4a7314dc4941b95a8b6e1f2fe37f
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06348032B1

Reaction notes

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