Hydrochloric Acid → (E)-3-(4-chloro-1-(2-chloro-4-(2-furyl)benzyl)-2-methylimidazol-5-yl)-2-propenic acid

HRID 1828814Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of methyl (E)-3-(4-chloro-1-(2-chloro-4-(2-furyl)benzyl)-2-methylimidazol-5-yl)-2-propenate (319 mg) in 1,4-dioxane (1.6 ml) was added 1N aqueous sodium hydroxide solution (1.2 ml) and the mixture was stirred at 50° C. for 1 hr. The reaction mixture was ice-cooled and 1N hydrochloric acid (1.2 ml) was added dropwise to neutralize the mixture. The resulting product was extracted 3 times with chloroform-methanol (4/1). The organic layers were combined, washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated to give (E)-3-(4-chloro-1-(2-chloro-4-(2-furyl)benzyl)-2-methylimidazol-5-yl)-2-propenic acid (310 mg) as a gray white powder.

Workup

temperaturecooled
extractionThe resulting product was extracted 3 times with chloroform-methanol (4/1)
washwashed with saturated brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated

Sources & evidence

ORD record: ord-1bab6c5950b74c0ab982cf06f1971622
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060721B1

Reaction notes

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