Trityl chloride → 2-Butyl-1-tritylimidazole-4,5-dicarbonitrile

HRID 53019Notes

Reaction equation

HRID 53019 reaction equation
[H-].[Na+].[CH2:3]([C:7]1[NH:8][C:9]([C:14]#[N:15])=[C:10]([C:12]#[N:13])[N:11]=1)[CH2:4][CH2:5][CH3:6].[C:16](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OCC)(=O)C>CN(C)C=O.O>[CH2:3]([C:7]1[N:11]([C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:10]([C:12]#[N:13])=[C:9]([C:14]#[N:15])[N:8]=1)[CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 6456Trityl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 52605912-butyl-1H-imidazole-4,5-dicarbonitrile

Product 1

HCID 190361382-Butyl-1-tritylimidazole-4,5-dicarbonitrileYield 82.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.25 g of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling, to a solution of 5 g of 2-butylimidazole-4,5-dicarbonitrile (prepared as described in Preparation 1) in 50 ml of N,N-dimethylformamide, and the resulting mixture was stirred for 15 minutes. 10 g of trityl chloride were then added, and the reaction mixture was stirred at 50° C. for 6 hours. At the end of this time, it was mixed with ethyl acetate and water, and the product was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:5 by volume mixture of ethyl acetate and hexane as the eluent, to give 9.83 g of the title compound as a syrup, which solidified on being allowed to stand. The solid melted at 144°-147° C. (with decomposition and coloration at 94°-98° C.).

Workup

  1. stirringthe reaction mixture was stirred at 50° C. for 6 hours
  2. extractionthe product was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-2521e937efa242b592f66820743fd951
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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