Chlorine → Clozylacon

HRID 2414136ノート

反応式

HRID 2414136 の反応式
[Cl:1]Cl.[CH3:3][O:4][CH2:5][C:6]([N:8]([CH:17]1[CH2:21][CH2:20][O:19][C:18]1=[O:22])[C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:16])=[O:7]>C(O)=O.[Fe](Cl)(Cl)Cl>[CH3:3][O:4][CH2:5][C:6]([N:8]([CH:17]1[CH2:21][CH2:20][O:19][C:18]1=[O:22])[C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([Cl:1])[C:10]=1[CH3:16])=[O:7]

参加物

5

反応物 2

HCID 24526Chlorine2 回HCID 155009N-(2,6-Dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)acetamide

生成物 1

HCID 93373Clozylacon収率 92.1%

試薬・触媒・溶媒 2

HCID 24380Iron chloride (FeCl3)触媒HCID 284Formic Acid溶媒

反応条件

温度
25 °C

実験手順

Over 2 hours, 74.6 g (1.05 moles) of chlorine are introduced at 25°-30° C. into a solution of 277 g (1.0 mole) of N-methoxyacetyl-N-(2-oxotetrahydro-3-furyl)-2,6-dimethylaniline and 5 g of iron(III) chloride in 300 ml of 85% formic acid. The reaction is exothermic and virtually no gas evolves. When the addition of chlorine is complete, the reaction mixture is stirred for 30 minutes at 25° C., the formic acid is then distilled off in vacuo, the residue is taken up in 500 ml of toluene and the toluenic solution is washed with 100 ml of water. The oily residue obtained after the toluene has been distilled off is crystallised from a mixture of isopropanol and hexane, affording 287 g (92% of theory) of N-methoxyacetyl-N-(2-oxotetrahydro-3-furyl)-3-chloro-2,6-dimethylaniline with a melting point of 80°-82° C.

後処理

  1. distillationthe formic acid is then distilled off in vacuo
  2. washthe toluenic solution is washed with 100 ml of water
  3. customThe oily residue obtained after the toluene
  4. distillationhas been distilled off
  5. customis crystallised from a mixture of isopropanol and hexane

出典と根拠

ORDレコード
ord-507652bfd56a4cb38292e04a74e21e9b
出典データセット
uspto-grants-1988_01
特許番号
US04721797

反応ノート

読み込み中…