Hydrochloric Acid → HCID 59240289, compound

HRID 1673031Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[N:9]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:12]=2[Cl:18])[CH:10]=1)=[O:5])C.CO.Cl>[OH-].[Na+].CCOC(C)=O>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([N:9]2[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=[C:8]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])=[C:12]([Cl:18])[CH:13]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a 250 mL round bottom flask was added 1-(4-Bromo-2-chloro-phenyl)-2-(2-chlorophenyl)-1H-imidazole-4-carboxylic acid ethyl ester (3.60 g, 8.18 mmol), MeOH (65 mL), and IN aq NaOH (41 mL). The reaction solution was allowed to stir at 50° C. for 2 hr. The reaction solution was diluted with EtOAc (200 mL), neutralized by the addition of aq 1 N HCl, and poured into a separatory funnel. The organic phase was partitioned, and the aqueous phase was and extracted with EtOAc (150 mL×2). The combined organic phases were dried over Na2SO4, filtered into a round bottom flask and concentrated on the Rotavapor. The crude residue was reprecipitated in an EtOAc/hexane solution and the solid precipitate was filtered under vacuum to afford 2.98 g (88% yield) of title product. MS (ESI) 410.3, 412.3, 414.3 [M+H]+.

Workup

additionpoured into a separatory funnel
customThe organic phase was partitioned
extractionextracted with EtOAc (150 mL×2)
dry with materialThe combined organic phases were dried over Na2SO4
filtrationfiltered into a round bottom flask
concentrationconcentrated on the Rotavapor
customThe crude residue was reprecipitated in an EtOAc/hexane solution
filtrationthe solid precipitate was filtered under vacuum

Sources & evidence

ORD record: ord-28e11eb8bbbf4574b678e75eba803e6f
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998995B2

Reaction notes

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