Dimethylformamide → HCID 67547593, compound

HRID 2356737Notes

Reaction equation

HRID 2356737 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](CC(N)=O)=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:12]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.C(O[CH2:32][CH3:33])(=O)C.C(=O)([O-])O.[Na+].C[N:40](C)C=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:10])[C:33]([C:32]#[N:40])=[C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 67546896HCID 67546896, compound

Product 1

HCID 67547593HCID 67547593, compound

Procedure

To a solution of 2-(4-chlorophenyl)-4-phenylimidazol-5-yl acetamide (10.00 g) in N,N-dimethylformamide (50 ml) was added dropwise 8.9 ml of phosphorus oxychloride (8.9 ml) below 20° C., and the mixture was stirred at room temperature for one hour. To the reaction mixture were added ice-water and ethyl acetate, and the mixture was neutralized by sodium hydrogen carbonate. The organic layer was collected, washed with brine, and dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was crystallized from diisopropyl ether to obtain 2-(4-chlorophenyl)-5-cyano-methyl-4-phenylimidazole (6.85 g).

Workup

  1. customThe organic layer was collected
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-7696d92909d445eeb3fcc094a22bd1bc
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

Loading…