4-Chloro-1-fluoro-2-nitrobenzene → 1-(4-Chloro-2-nitrophenyl)-2-isopropyl-1H-imidazole

HRID 72755

反応式

HRID 72755 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH:12]([C:15]1[NH:16][CH:17]=[CH:18][N:19]=1)([CH3:14])[CH3:13].C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:16]2[CH:17]=[CH:18][N:19]=[C:15]2[CH:12]([CH3:14])[CH3:13])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

参加物

5

反応物 3

HCID 676604-Chloro-1-fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 1234571H-Imidazole, 2-(1-methylethyl)-

生成物 1

HCID 591988521-(4-Chloro-2-nitrophenyl)-2-isopropyl-1H-imidazole収率 64.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 4-chloro-1-fluoro-2-nitrobenzene 1.01 g, 2-isopropylimidazole 634 mg, N,N-diisopropylethylamine, 1.46 mL and acetonitrile 12 mL was heated under reflux for 15 hours. The solvent was distilled off and water was added to the residue which was then rendred acidic with diluted hydrochloric acid. After washing the same with diethyl ether, the aqueous layer was rendered alkaline with aqueous sodium hydroxide solution and extracted twice with chloroform. The organic layer was washed with water, dried over magnesium sulfate, and removed of the solvent by distillation to provide 0.98 g of the title compound.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. distillationThe solvent was distilled off
  4. additionwater was added to the residue which
  5. washAfter washing the same with diethyl ether
  6. extractionextracted twice with chloroform
  7. washThe organic layer was washed with water
  8. dry with materialdried over magnesium sulfate
  9. customremoved of the solvent by distillation

出典と根拠

ORDレコード
ord-dc85e8bc09d24cedbfdd0e9b5eb4d8c7
出典データセット
uspto-grants-2014_09
特許番号
US08829000B2

関連ノート

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