1H-1,2,4-Triazole → 5-Chloro-2-(1H-1,2,4-triazol-1-YL)benzonitrile

HRID 857721

반응식

HRID 857721 반응식
Cl[C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[Cs+].[Cs+].[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1>CN(C=O)C.O>[Cl:10][C:7]1[CH:8]=[CH:9][C:2]([N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)=[C:3]([CH:6]=1)[C:4]#[N:5]

참가 물질

6

반응물 3

HCID 92571H-1,2,4-Triazole2회HCID 10796Cesium carbonateHCID 890002,5-Dichlorobenzonitrile

생성물 1

HCID 218662965-Chloro-2-(1H-1,2,4-triazol-1-YL)benzonitrile

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

실험 절차

To a solution of 2,5-dichlorobenzonitrile (10 g, 58.1 mmol) in DMF (100 ml) is added cesium carbonate (22.7 g, 69.8 mmol) and 1,2,4-triazole (4.8 g, 69.8 mmol) and the reaction mixture is stirred at 65° C. for 5.5 h, at 75° C. for 16 h, at 85° C. for 7 h. More 1,2,4-triazole (5 g) is added and the reaction mixture is stirred at 85° C. for 18 h and at 100° C. for 4 h. After cooling to room temperature, the mixture is diluted with water and extracted with EtOAc 3 times. The combined organic layer is washed with aqueous LiCl, dried on sodium sulfate, concentrated in vacuo to give 5-Chloro-2-[1,2,4]triazol-1-yl-benzonitrile as a white solid which is used in the next step without further purification.

후처리

  1. stirringthe reaction mixture is stirred at 85° C. for 18 h and at 100° C. for 4 h
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with EtOAc 3 times
  4. washThe combined organic layer is washed with aqueous LiCl
  5. customdried on sodium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-01ecf9e1acc04013ba1d817e55c02779
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144899B2

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