2-Butyl-5-cyano-4-(1-hydroxy-1-methylethyl)-1-tritylimidazole → HCID 178441634, compound

HRID 53024Notes

Reaction equation

HRID 53024 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:14]#[N:15])=[C:8]([C:10]([OH:13])([CH3:12])[CH3:11])[N:9]=1)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C>[CH2:1]([C:5]1[NH:6][C:7]([C:14]#[N:15])=[C:8]([C:10]([OH:13])([CH3:11])[CH3:12])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 190362212-Butyl-5-cyano-4-(1-hydroxy-1-methylethyl)-1-tritylimidazole

Product 1

HCID 178441634HCID 178441634, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1.3 g of 2-butyl-5-cyano-4-(1-hydroxy-1-methylethyl)-1-tritylimidazole [prepared as described in step (i) above] and 26 ml of 75% v/v aqueous acetic acid was stirred at 50° C. for 3 hours, and then the solvent was removed by distillation under reduced pressure. The resulting residue was washed with carbon tetrachloride and purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, and the product was crystallized in carbon tetrachloride, to give 0.6 g of the title compound as colorless crystals, melting at 171°-172° C.

Workup

  1. customthe solvent was removed by distillation under reduced pressure
  2. washThe resulting residue was washed with carbon tetrachloride
  3. custompurified by column chromatography through silica gel
  4. additionby volume mixture of methylene chloride and methanol as the eluent
  5. customthe product was crystallized in carbon tetrachloride

Sources & evidence

ORD record
ord-468502faa0154e0194dc0ffe37181b73
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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