3-Fluorobenzoyl chloride → N-(5-Cyano-1H-imidazol-4-yl)-3-fluorobenzamide

HRID 1285219

Reaction equation

HRID 1285219 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]#[N:8].[F:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](Cl)=[O:14]>N1C=CC=CC=1>[C:7]([C:6]1[NH:5][CH:4]=[N:3][C:2]=1[NH:1][C:13](=[O:14])[C:12]1[CH:16]=[CH:17][CH:18]=[C:10]([F:9])[CH:11]=1)#[N:8]

Participants

4

Reactant 2

HCID 743763-Fluorobenzoyl chlorideHCID 787775-amino-1H-imidazole-4-carbonitrile

Product 1

HCID 13588448N-(5-Cyano-1H-imidazol-4-yl)-3-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under a nitrogen atmosphere a stirred solution of 4-amino-1H-imidazole-5-carbonitrile (1.1 g, 0.01 mole) and 3-fluorobenzoyl chloride (1.8 g, 0.011 mole) in 25 ml of dry pyridine was heated at reflux for one hour. The reaction mixture was cooled and the pyridine removed under reduced pressure. The residue was washed with saturated aqueous sodium bicarbonate and water. The residual solid was collected by filtration and washed sequentially with two portions of water, diethyl ether, and ethyl acetate. The solid was dried under reduced pressure; mp, 222°-240°. The solid was dissolved in ethanol and precipitated with petroleum ether, then collected by filtration and washed with diethyl ether to give after drying N-(5-cyano-1H-imidazol-4-yl)-3-fluorobenzamide (2.0 g; mp, 242°-46°).

Workup

  1. temperatureat reflux for one hour
  2. temperatureThe reaction mixture was cooled
  3. customthe pyridine removed under reduced pressure
  4. washThe residue was washed with saturated aqueous sodium bicarbonate and water
  5. filtrationThe residual solid was collected by filtration
  6. washwashed sequentially with two portions of water, diethyl ether, and ethyl acetate
  7. customThe solid was dried under reduced pressure
  8. custommp, 222°-240°
  9. dissolutionThe solid was dissolved in ethanol
  10. customprecipitated with petroleum ether
  11. filtrationcollected by filtration
  12. washwashed with diethyl ether
  13. customto give
  14. dry with materialafter drying N-(5-cyano-1H-imidazol-4-yl)-3-fluorobenzamide (2.0 g; mp, 242°-46°)

Sources & evidence

ORD record
ord-9c3ef748d9a947a0a6cda1e27811b3b8
Source dataset
uspto-grants-1986_01
Patent number
US04565875

Linked notes

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