Water → 2-Methyl-4-((1-(trifluoromethyl)cyclopropyl)methyl)-1-trityl-1H-imidazole

HRID 216313Notes

Reaction equation

O.NN.[CH3:4][C:5]1[N:6]([C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[C:8]([C:10]([C:12]2([C:15]([F:18])([F:17])[F:16])[CH2:14][CH2:13]2)=O)[N:9]=1.[OH-].[K+].O>C(O)CO>[CH3:4][C:5]1[N:6]([C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:7]=[C:8]([CH2:10][C:12]2([C:15]([F:16])([F:17])[F:18])[CH2:13][CH2:14]2)[N:9]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Hydrazine hydrate (30 mL) was added to a solution of (2-methyl-1-trityl-1H-imidazol-4-yl)[1-(trifluoromethyl)cyclopropyl]methanone (15.78 g, 34.2 mmol) and powdered potassium hydroxide (9.6 g, 171 mmol) in ethylene glycol (200 mL). After stirring at 120° C. for 20 min, the reaction mixture was heated at 180° C. for 2 h. After cooling to ambient temperature, water was added and the mixture was extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-60% ethyl acetate/hexane afforded the title compound.

Workup

temperaturethe reaction mixture was heated at 180° C. for 2 h
temperatureAfter cooling to ambient temperature
extractionthe mixture was extracted twice with ethyl acetate
washThe combined organic extracts were washed with brine
dry with materialdried (sodium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2d6e0de9f81e4ca2bfb4d225650cd940
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193228B2

Reaction notes

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