Trifluoromethylsulfinylchloride → 5-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrile

HRID 919169노트

반응식

HRID 919169 반응식
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([F:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[CH:3]=1.S(C1C=CC(C)=CC=1)(O)(=O)=O.CNC.[C:35]([S:39](Cl)=[O:40])([F:38])([F:37])[F:36]>C1(C)C=CC=CC=1>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([F:13])=[CH:11][C:10]([C:14]([F:16])([F:15])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:39]([C:35]([F:38])([F:37])[F:36])=[O:40]

참가 물질

5

반응물 3

HCID 11008121TrifluoromethylsulfinylchlorideHCID 12199009Dimethylamine p-toluenesulfonateHCID 684093715-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)-phenyl)-1H-pyrazole-3-carbonitrile

생성물 1

HCID 898587905-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrile수율 64.6%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
40 °C

실험 절차

To a solution of 5-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile (140 g, 459.6 mmol, 1.00 eq.) and dimethylamine tosylate (151.8 g, 698.6 mmol, 1.52 eq.) in toluene (840 mL) was added CF3SOCl (89.7 g, 588.3 mmol, 1.28 eq.). After the mixture was stirred at 40° C. for 16 h, nitrogen was bubbled through the solution and the solution was cooled to rt. Then the mixture was poured into 2 L ice/water and stirred at 0° C. for 1 h. The precipitated solid was isolated by filtration and dried under vacuum. The solid was recrystallized with toluene to give 5-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrile (125 g, 64%) as yellow solid.

후처리

  1. customnitrogen was bubbled through the solution
  2. temperaturethe solution was cooled to rt
  3. additionThen the mixture was poured into 2 L ice/water
  4. stirringstirred at 0° C. for 1 h
  5. customThe precipitated solid was isolated by filtration
  6. customdried under vacuum
  7. customThe solid was recrystallized with toluene

출처 및 근거

ORD 기록
ord-9dac93fa030f492ba721f2b855d99919
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273007B2

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