Benzimidazole → HCID 67781271, compound

HRID 1742356Notes

Reaction equation

HRID 1742356 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.BrC[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1>CN(C)C=O>[CH3:2][C:14]1[CH:13]=[CH:12][CH:19]=[CH:18][C:15]=1[C:16]#[N:17].[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 5798BenzimidazoleHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 67781271HCID 67781271, compoundYield 141.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using the procedure of Step B of Example 1, 951 mg of benzimidazole and 1.97 g of 4-bromomethyl benzonitrile in dimethylformamide were reacted to obtain 2.48 g of crude product which was chromatographed on silica (eluant: methylene chloride - methanol (95-5)) to obtain 1.34 g of the desired product melting at 94° C. after crystallization from ether. An analytical sample was prepared by two successive crystallizations of 422 mg of the product from ether, then from isopropyl ether to obtain 167 mg of pure product melting at 94° C.

Workup

  1. customwere reacted
  2. customto obtain 2.48 g of crude product which
  3. customwas chromatographed on silica (eluant: methylene chloride - methanol (95-5))

Sources & evidence

ORD record
ord-3bc303e4d67e47c88bccd10edd540b71
Source dataset
uspto-grants-1994_08
Patent number
US05338756

Reaction notes

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