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

HRID 889546

반응식

HRID 889546 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 8900Heptane용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-7332f793a6874445b5f40ea32fa9a0de
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252875B2

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