2-Butyl-5-cyano-4-(1-hydroxy-1-methylpropyl)-1-tritylimidazole → HCID 178441653, compound

HRID 265169Notes

Reaction equation

[CH2:1]([C:5]1[N:6](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:7]([C:15]#[N:16])=[C:8]([C:10]([OH:14])([CH3:13])[CH2:11][CH3:12])[N:9]=1)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C>[CH2:1]([C:5]1[NH:6][C:7]([C:15]#[N:16])=[C:8]([C:10]([OH:14])([CH3:13])[CH2:11][CH3:12])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1.21 g of 2-butyl -5-cyano-4-(1-hydroxy-1-methyl propyl)-1-tritylimidazole (prepared as described in Preparation 17) and 20 ml of 75% v/v aqueous acetic acid was stirred at 50° C. for 1 hour, after which the mixture was cooled, and the deposited crystals of trityl alcohol were removed by filtration. The filtrate was concentrated by evaporation under reduced pressure, and the remaining water and acetic acid were distilled off as a toluene azeotrope under reduced pressure. The residue was purified by column chromatography through silica gel, using a 9:1 by volume mixture of methylene chloride and methanol as the eluent, to give 0.47 g of the title compound as a crystalline powder, melting at 139°-142° C.

Workup

temperatureafter which the mixture was cooled
customthe deposited crystals of trityl alcohol were removed by filtration
concentrationThe filtrate was concentrated by evaporation under reduced pressure
distillationthe remaining water and acetic acid were distilled off as a toluene azeotrope under reduced pressure
customThe residue was purified by column chromatography through silica gel
additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record: ord-b0b2a0f0438f4b4098f839d6b3fed369
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05646171

Reaction notes

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