Lithium hydroxide, monohydrate → Lithium 2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylate

HRID 75491Notes

Reaction equation

[CH3:1][C:2]1[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4]([CH3:12])=[C:5]([C:7]([O:9]CC)=[O:8])[N:6]=1.O.[OH-].[Li+:21]>C1COCC1.O>[CH3:1][C:2]1[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4]([CH3:12])=[C:5]([C:7]([O-:9])=[O:8])[N:6]=1.[Li+:21]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of ethyl 2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylate (compound 12a, 4.97 g, 20.3 mmol) in THF/water (15/15 mL) was added lithium hydroxide monohydrate at room temperature. The reaction mixture was stirred at 55° C. for 12 hrs, then the mixture was concentrated in vacuo. The crude solid was washed with diethyl ether to provide the title compound (4.06 g, 90%) as a white solid. The obtained product was used for the next step without purification.

Workup

concentrationthe mixture was concentrated in vacuo
washThe crude solid was washed with diethyl ether

Sources & evidence

ORD record: ord-e23872cdbe2244a4bb327c766011f15b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835436B2

Reaction notes

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