4-Benzoyl-2-butyl-5-cyano-1-tritylimidazole → HCID 178441735, compound

HRID 265160Notes

Reaction equation

[C:1]([C:9]1[N:10]=[C:11]([CH2:35][CH2:36][CH2:37][CH3:38])[N:12](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:13]=1[C:14]#[N:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C>[C:1]([C:9]1[N:10]=[C:11]([CH2:35][CH2:36][CH2:37][CH3:38])[NH:12][C:13]=1[C:14]#[N:15])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 10.3 g of 4-benzoyl-2-butyl-5-cyano-1-tritylimidazole [prepared as described in step (i) above] in 80% v/v aqueous acetic acid was stirred at 60° C. for 5 hours. At the end of this time, the solution thus obtained was concentrated by evaporation under reduced pressure, and 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. The resulting oily product was dissolved in carbon tetrachloride and the solution was allowed to stand at room temperature, to precipitate crystals, which were collected by filtration to give 4.46 g of the title compound, melting at 121°-122° C.

Workup

customAt the end of this time, the solution thus obtained
concentrationwas concentrated 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
dissolutionThe resulting oily product was dissolved in carbon tetrachloride
customto stand at room temperature
customto precipitate crystals, which
filtrationwere collected by filtration

Sources & evidence

ORD record: ord-9e45716133c14a5d9429b41608e61ba6
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05646171

Reaction notes

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