Ammonium Chloride → 2-Butyl-5-cyano-4-(1-hydroxy-1-methylethyl)-1-tritylimidazole

HRID 53023Notes

Reaction equation

[CH3:1][Mg]I.[C:4]([C:7]1[N:8]=[C:9]([CH2:33][CH2:34][CH2:35][CH3:36])[N:10]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]=1[C:12]#[N:13])(=[O:6])[CH3:5].[Cl-].[NH4+]>O1CCCC1>[CH2:33]([C:9]1[N:10]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:11]([C:12]#[N:13])=[C:7]([C:4]([OH:6])([CH3:1])[CH3:5])[N:8]=1)[CH2:34][CH2:35][CH3:36]

Participants

Conditions

Temperature: 40 °C

Procedure

1 ml of a 2M solution of methylmagnesium iodide in tetrahydrofuran was added dropwise at room temperature, whilst stirring, to a solution of 840 mg of 4-acetyl-2-butyl-5-cyano-1-tritylimidazole [prepared as described in Preparation 5(ii)] in 15 ml of tetrahydrofuran, and the resulting mixture was stirred at 40° C. for 1 hour. The mixture was cooled, and then a saturated aqueous solution of ammonium chloride was added to it dropwise. The tetrahydrofuran layer was separated and concentrated by evaporation under reduced pressure. The concentrate was purified by column chromatography through silica gel, using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 539 mg of the title compound as a colorless solid, melting at 151°-152° C.

Workup

temperatureThe mixture was cooled
customThe tetrahydrofuran layer was separated
concentrationconcentrated by evaporation under reduced pressure
customThe concentrate was purified by column chromatography through silica gel
additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record: ord-56c2775e83704fca903ab9751772b843
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616599

Reaction notes

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