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

HRID 1871564ノート

反応式

HRID 1871564 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a8f634da22cf492aab7816420f95b482
出典データセット
uspto-grants-2000_08
特許番号
US06103750

反応ノート

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