Benzimidazole → Lithium benzimidazolate

HRID 23311

Reaction equation

HRID 23311 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[Li:10]CCCC>C1(C)C=CC=CC=1>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N-:3][CH:2]=1.[Li+:10]

Participants

4

Reactant 2

HCID 5798BenzimidazoleHCID 178418339Butyllithium

Product 1

HCID 12985676Lithium benzimidazolate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A slurry of benzimidazole (8.50 g, 36.3 mmol) in toluene (40 mL) at 0° C. was treated with 25.8 mL of a 2.8 M n-BuLi (72.2 mmol) solution in hexanes. This solution mixture was then refluxed for one day during which time the slurry became off-white. The slurry was then filtered over a medium glass frit and dried to give a white solid.

Workup

  1. temperatureThis solution mixture was then refluxed for one day during which time the slurry
  2. filtrationThe slurry was then filtered over a medium glass frit
  3. customdried
  4. customto give a white solid

Sources & evidence

ORD record
ord-a3fec071d6a44a0a9e0f5f1bd556fe97
Source dataset
uspto-grants-2005_02
Patent number
US06852446B2

Linked notes

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