Hydrochloric Acid → 6-Benzenesulfonylcarbamoyl-1-(2,4-difluorobenzyl)-2-methyl-benzimidazole

HRID 1699626Notes

Reaction equation

[C:1]1([S:7]([NH:10][C:11](=[O:32])[C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=O)[CH3:20])=[C:14]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[F:31])[CH:13]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CO.C(=O)(O)[O-].[K+]>O>[C:1]1([S:7]([NH:10][C:11]([C:12]2[CH:17]=[CH:16][C:15]3[N:18]=[C:19]([CH3:20])[N:22]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=4[F:31])[C:14]=3[CH:13]=2)=[O:32])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

N-benzenesulfonyl-4-acetylamino-3-(2,4-difluorobenzylamino)benzamide (0.370 g) is added to a mixture solvent of 10% hydrochloric acid (3.3 g), methanol (6 ml), and water (4 ml). Furthermore, 35% hydrochloric acid (0.5 g) is added and the solution is stirred for three hours at 60° C. After 20% potassium bicarbonate aqueous solution is added to turn the reaction solution into a basic, its acidity is adjusted to pH 5˜6 with 10% hydrochloric acid. Precipitated crystals are separated through filtration, dried and thus, 0.182 g of 6-benzenesulfonylcarbamoyl-1-(2,4-difluorobenzyl)-2-methyl-benzimidazole is obtained. 1H-NMR (DMSO-d6, δ): 2.53 (3H, s), 5.56 (2H, s), 6.95-7.01 (1H, m), 7.04 (1H, dt, J=8.7 and 1.4 Hz), 7.32 (1H, dt, J=10.7 and 2.1 Hz), 7.59-7.66 (3H, m), 7.68-7.74 (2H, m), 8.00 (2H, d, J=8.1 Hz), 8.13 (1H, s), 12.43 (1H, s).

Workup

customPrecipitated crystals
customare separated through filtration
customdried

Sources & evidence

ORD record: ord-f44ab3188c754392974940d3c95456d8
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06348032B1

Reaction notes

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