Sodium Hydroxide → 2-chloro-5-(4-methoxybutyl)-1-phenyl-1H-imidazole-4-carboxylic acid

HRID 1509553Notes

Reaction equation

[Cl:1][C:2]1[N:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:4]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])=[C:5]([C:7]([O:9]C)=[O:8])[N:6]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[N:3]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:4]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 2-chloro-5-(4-methoxybutyl)-1-phenyl-1H-imidazole-4-carboxylate (450 mg) was dissolved in methanol (5 ml), 1M aqueous sodium hydroxide solution (4.2 ml) was added and the mixture was stirred at 80° C. for 2 hr. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was acidified with 1M hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (372 mg).

Workup

temperatureAfter cooling to room temperature
concentrationthe reaction mixture was concentrated under reduced pressure
extractionextracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-101ce1ea9fc045b7a10a187773e61e90
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221836B2

Reaction notes

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