Thionyl Chloride → 5-Amino-1-(6-chloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)-4-trifluoromethylsulfenylpyrazole

HRID 1871567노트

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HRID 1871567 반응식
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:15]=2[Cl:16])[C:12]([F:18])([F:17])[O:11][C:10]3([F:20])[F:19])[N:5]=[CH:4][CH:3]=1.[F:21][C:22]([F:27])([F:26])[S:23]([O-])=O.[Na+].S(C1C=CC(C)=CC=1)(O)(=O)=O.CNC.S(Cl)(Cl)=O>C1(C)C=CC=CC=1.O>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:15]=2[Cl:16])[C:12]([F:18])([F:17])[O:11][C:10]3([F:20])[F:19])[N:5]=[CH:4][C:3]=1[S:23][C:22]([F:27])([F:26])[F:21]

참가 물질

7

반응물 4

HCID 24386Thionyl ChlorideHCID 12199009Dimethylamine p-toluenesulfonateHCID 186915105-Amino-1-(6-chloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)pyrazoleHCID 23690734Sodium trifluoromethanesulfinate

생성물 1

HCID 186915325-Amino-1-(6-chloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)-4-trifluoromethylsulfenylpyrazole수율 38.6%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

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온도
55 °C

실험 절차

To a suspension wherein 5-amino-1-(6-chloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)pyrazole (391 mg, 1.27 mmol), sodium trifluromethanesulfinate (397 mg, 2.54 mmol) and dimethylamine tosylate (690 mg, 3.17 mmol) are in toluene (4 ml), thionyl chloride (302 mg, 2.54 mmol) was added dropwise under ice cooling over a period of about 10 minutes and then stirred under heating at 50 to 60° C. for 14 hours. After allowing to cool, the reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel column chromatography to give 200 mg of 5-amino-1-(6-chloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)-4-trifluoromethylsulfenylpyrazole.

후처리

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-180381f3d4aa4e70b4c250ade5eca81e
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06103750

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