Imidazole → 4-(2-Imidazolylacetyl)benzenecarbonitrile

HRID 31757Notes

Reaction equation

HRID 31757 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=1)=[O:4].[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1>CC#N.ClCCl.O>[NH:13]1[CH:17]=[CH:16][N:15]=[C:14]1[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 2

HCID 795ImidazoleHCID 142493Benzonitrile, 4-(chloroacetyl)-

Product 1

HCID 221429994-(2-Imidazolylacetyl)benzenecarbonitrileYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 4-(2-chloroacetyl)benzenecarbonitrile (0.5 M) and imidazole (1.5 M) in CH3CN (200 ml) were heated for 14 hours at 60° C. The product was stripped of solvent under reduced pressure. The residue was diluted with dichloromethane (250 ml) and water (100 ml), and the mixture was stirred for 30 min. After filtering off a solid impurity, the aqueous layer was removed and discarded. The organic layer was washed sequentially with water (60 ml), sat. aq. NaHCO3 (60 ml), water (60 ml), brine (60 ml), dried with Na2SO4, filtered, and concentrated under reduced pressure. The dark colored oil was dried overnight in vacuo giving 4-(2-imidazolylacetyl)benzenecarbonitrile in 90% yield.

Workup

  1. filtrationAfter filtering off a solid impurity
  2. customthe aqueous layer was removed
  3. washThe organic layer was washed sequentially with water (60 ml), sat. aq. NaHCO3 (60 ml), water (60 ml), brine (60 ml)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe dark colored oil was dried overnight in vacuo

Sources & evidence

ORD record
ord-8a00c94f26fa44bab243eb0d727978c8
Source dataset
uspto-grants-2008_09
Patent number
US07425557B2

Reaction notes

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