Hydrochloric Acid → 2-[4-(4-Acetyl-3-hydroxy-2-propylphenylthio)butylthio]benzimidazole-5-carboxylic acid

HRID 2165941Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][C:16]2[NH:17][C:18]3[CH:24]=[C:23]([C:25]([O:27]CC)=[O:26])[CH:22]=[CH:21][C:19]=3[N:20]=2)=[C:6]([CH2:30][CH2:31][CH3:32])[C:5]=1[OH:33])(=[O:3])[CH3:2].O1CCOCC1.[OH-].[Na+].Cl>O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][C:16]2[NH:17][C:18]3[CH:24]=[C:23]([C:25]([OH:27])=[O:26])[CH:22]=[CH:21][C:19]=3[N:20]=2)=[C:6]([CH2:30][CH2:31][CH3:32])[C:5]=1[OH:33])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl 2-[4-(4-acetyl-3-hydroxy-2-propylphenylthio)butylthio]benzimidazole-5-carboxylate (2.50 g), 1,4-dioxane (30 ml) and sodium hydroxide (1.03 g) in water (30 ml) was stirred at 60 ° C. for 2 hours. This mixture was poured into ice-water, made acidic with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography, eluting with dichloromethane-methanol (10:1), to give the title compound (1.52 g, 64.5 %) as yellow crystals, mp 90-95° C.

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous sodium sulfate
customevaporated
customThe resulting residue was purified by silica gel column chromatography
washeluting with dichloromethane-methanol (10:1)

Sources & evidence

ORD record: ord-9ee0480b8dd148b2a130feb0005107be
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04942245

Reaction notes

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