4-Chloroaniline → N-(4-chlorophenyl)-4-pyridinecarboxamide-1-oxide

HRID 568401

反応式

HRID 568401 の反応式
C(N1C=CN=C1)(N1C=CN=C1)=O.[N+:13]1([O-:22])[CH:18]=[CH:17][C:16]([C:19]([OH:21])=O)=[CH:15][CH:14]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1>CN(C)C=O>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:19]([C:16]2[CH:15]=[CH:14][N+:13]([O-:22])=[CH:18][CH:17]=2)=[O:21])=[CH:26][CH:25]=1

参加物

5

反応物 3

HCID 78124-ChloroanilineHCID 261304-Pyridinecarboxylic acid, 1-oxideHCID 682631,1'-Carbonyldiimidazole

生成物 1

HCID 13003309N-(4-chlorophenyl)-4-pyridinecarboxamide-1-oxide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

1,1'-Carbonyldiimidazole (3.829 g, 23.6 mmol) was added to a suspension of 4-pyridinecarboxylic acid-1-oxide (2.986 g, 21.5 mmol) in dry dimethylformamide (50 ml) and the resulting solution was stirred for 45 minutes and treated with a solution of 4-chlorobenzenamine (3.012 g, 23.6 mmol) in dry dimethylformamide (20 ml). After 18 hours, the solution was evaporated in vacuo to give an oil which slowly solidified. The solid was recrystallised from ethyl acetate-cyclohexane and suspended in saturated aqueous sodium bicarbonate solution. The mixture was stirred vigorously for 20 minutes, filtered, and the crystals washed with water (3×10 ml) and ethanol (3×10 ml) and dried in vacuo to give the title compound as a quarter hydrate (1.614 g), m.p. 247°-249°.

後処理

  1. waitAfter 18 hours
  2. customthe solution was evaporated in vacuo
  3. customto give an oil which
  4. customThe solid was recrystallised from ethyl acetate-cyclohexane
  5. stirringThe mixture was stirred vigorously for 20 minutes
  6. filtrationfiltered
  7. washthe crystals washed with water (3×10 ml) and ethanol (3×10 ml)
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-809a93e17f324e09927b098a9783039d
出典データセット
uspto-grants-1988_03
特許番号
US04728658

関連ノート

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