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

HRID 1871564노트

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HRID 1871564 반응식
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:15]=2[F:16])[C:12]([F:18])([F:17])[O:11][C:10]3([F:20])[F:19])[N:5]=[C:4]([C:21]#[N:22])[CH:3]=1.[F:23][C:24]([F:29])([F:28])[S:25]([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[F:16])[C:12]([F:18])([F:17])[O:11][C:10]3([F:20])[F:19])[N:5]=[C:4]([C:21]#[N:22])[C:3]=1[S:25][C:24]([F:29])([F:28])[F:23]

참가 물질

7

반응물 4

HCID 24386Thionyl ChlorideHCID 12199009Dimethylamine p-toluenesulfonateHCID 186915345-Amino-3-cyano-1-(6-fluoro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)pyrazoleHCID 23690734Sodium trifluoromethanesulfinate

생성물 1

HCID 186915225-Amino-3-cyano-1-(6-fluoro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)-4-trifluoromethylsulfenylpyrazole수율 28.7%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

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온도
55 °C

실험 절차

To a suspension wherein 5-amino-3-cyano-1-(6-fluoro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)pyrazole (900 mg, 2.85 mmol), sodium trifluoromethanesulfinate (890 mg, 5.70 mmol) and dimethylamine tosylate (1.550 g, 7.13 mmol) are in toluene (5 ml), thionyl chloride (678 mg, 5.70 mmol) was added dropwise under ice cooling over a period of about 10 minutes and stirred at 50 to 60° C. for 10 hours. After allowing time 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 340 mg of 5-amino-3-cyano-1-(6-fluoro-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-a8f634da22cf492aab7816420f95b482
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06103750

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