Water → 1-{6-[1-(2-Chloro-4,6-dimethylphenylimino)ethyl]pyridin-2-yl}ethanone

HRID 889546

反応式

HRID 889546 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH3:11])[N:5]=1)(=[O:3])[CH3:2].[Cl:13][C:14]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:15]=1[NH2:16].O>CCCCCCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:13][C:14]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:15]=1[N:16]=[C:10]([C:6]1[N:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:9]=[CH:8][CH:7]=1)[CH3:11]

参加物

6

反応物 3

HCID 962WaterHCID 707902,6-DiacetylpyridineHCID 1130332-Chloro-4,6-dimethylaniline

生成物 1

HCID 594646241-{6-[1-(2-Chloro-4,6-dimethylphenylimino)ethyl]pyridin-2-yl}ethanone収率 35%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 8900Heptane溶媒

実験手順

20 g of 2,6-diacetylpyridine (0.123 mol), 19.08 g of 2-chloro-4,6-dimethylaniline (0.123 mol) and 0.5 g of p-toluenesulfonic acid were heated under reflux on a water separator in 500 ml of heptane for 75 min. The insoluble solid was filtered off. The solvent was distilled off from the filtrate down to 150 ml, and the remaining filtrate was cooled to room temperature, while stirring. 25.3 g of a yellow solid precipitated out. This was filtered off and recrystallized from 60 ml of hot isopropanol. A total of 12.9 g (0.043 mol) of 1-{6-[1-(2-chloro-4,6-dimethylphenylimino)ethyl]-pyridin-2-yl}ethanone were obtained in a yield of 35%.

後処理

  1. filtrationThe insoluble solid was filtered off
  2. distillationThe solvent was distilled off from the filtrate down to 150 ml
  3. custom25.3 g of a yellow solid precipitated out
  4. filtrationThis was filtered off
  5. customrecrystallized from 60 ml of hot isopropanol

出典と根拠

ORDレコード
ord-7332f793a6874445b5f40ea32fa9a0de
出典データセット
uspto-grants-2012_08
特許番号
US08252875B2

関連ノート

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