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

HRID 1285219

反応式

HRID 1285219 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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°).

後処理

  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°)

出典と根拠

ORDレコード
ord-9c3ef748d9a947a0a6cda1e27811b3b8
出典データセット
uspto-grants-1986_01
特許番号
US04565875

関連ノート

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