Benzimidazole → HCID 67781271, compound

HRID 274332Notes

Reaction equation

HRID 274332 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-7112b97b040744008a1ea12ff3a7befe
Source dataset
uspto-grants-1995_02
Patent number
US05389634

Reaction notes

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