Water → HCID 178496035, compound

HRID 1639549Notes

Reaction equation

[OH:1][C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:7]([NH:9][C:10]([NH:12][CH2:13][CH2:14][O:15][CH3:16])=[O:11])=[N:8][C:4]=2[CH:3]=1.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[S:27](Cl)(=[O:29])=[O:28].O>[OH-].[Na+]>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[S:27]([O:1][C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:7]([NH:9][C:10](=[O:11])[NH:12][CH2:13][CH2:14][O:15][CH3:16])=[N:8][C:4]=2[CH:3]=1)(=[O:29])=[O:28]

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 175 mg of 1-(5-hydroxy-1H-benzimidazol-2-yl)-3-(2-methoxyethyl)urea in 15 cm3 of 0.1N aqueous sodium hydroxide solution are added 189 mg of finely ground 2,6-dichlorobenzenesulfonyl chloride. The suspension is stirred for about 20 hours at a temperature in the region of 20° C., 10 cm3 of water are then added and the mixture is cooled to about 5° C. for about 15 minutes. The precipitate is filtered off by suction, washed with three times 2 cm3 of water and dried under reduced pressure (13 kPa) over phosphorus pentoxide. After flash chromatography on a column of silica [eluent: dichloromethane/methanol/acetonitrile (95/3/2 by volume)], 65 mg of 2-{[(2-methoxyethyl)carbamoyl]amino}-1H-benzimidazol-5-yl 2,6-dichlorobenzenesulfonate are obtained in the form of a cream-coloured powder, the characteristics of which are as follows:

Workup

additionare then added
filtrationThe precipitate is filtered off by suction
washwashed with three times 2 cm3 of water
dry with materialdried under reduced pressure (13 kPa) over phosphorus pentoxide

Sources & evidence

ORD record: ord-9a2bdd8081fe4db59f67a899490d994e
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110571B2

Reaction notes

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