Pyrazole → 4,4,5,8-Tetramethyl-6-(1-ethyl-5-ethanesulfonyloxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide

HRID 1069

反応式

HRID 1069 の反応式
[CH3:1][C:2]1([CH3:26])[C:11]2[C:6](=[C:7]([CH3:23])[CH:8]=[C:9]([C:13]([C:15]3[CH:16]=[N:17][N:18]([CH2:21][CH3:22])[C:19]=3[OH:20])=[O:14])[C:10]=2[CH3:12])[S:5](=[O:25])(=[O:24])[CH2:4][CH2:3]1.N1C=CC=N1.C(=O)([O-])[O-].[K+].[K+].[CH2:38]([S:40](Cl)(=[O:42])=[O:41])[CH3:39]>C(Cl)Cl.O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH3:26][C:2]1([CH3:1])[C:11]2[C:6](=[C:7]([CH3:23])[CH:8]=[C:9]([C:13]([C:15]3[CH:16]=[N:17][N:18]([CH2:21][CH3:22])[C:19]=3[O:20][S:40]([CH2:38][CH3:39])(=[O:42])=[O:41])=[O:14])[C:10]=2[CH3:12])[S:5](=[O:25])(=[O:24])[CH2:4][CH2:3]1

参加物

8

反応物 4

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 11667Ethanesulfonyl chlorideHCID 178418286HCID 178418286、化合物

生成物 1

HCID 154773584,4,5,8-Tetramethyl-6-(1-ethyl-5-ethanesulfonyloxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide収率 82%

試薬・触媒・溶媒 3

HCID 66133Benzyl triethylammonium chloride触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

0.7 Gram (1.9 mmol) of the 4,4,5,8-tetramethyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound Ic-1) corresponding to pyrazole derivative (I-H), obtained in Referential Production Example 5, was dissolved in 8 ml of methylene chloride. Then, a solution of 0.51 g (3.8 mmol) of potassium carbonate in 5 ml of water was added, and further, 0.49 g (3.8 mmol) of ethanesulfonyl chloride and 0.05 g (0.2 mmol) of benzyltriethylammonium chloride, corresponding to compound B-A-Hal, were added. The mixture was allowed to react at room temperature for 2 hours, and further refluxed under heat for 2 hours. The reaction mixture was allowed to cool, and then a methylene chloride layer was recovered and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant oil was purified by silica gel column chromatography to give 0.73 g (yield 82%) of 4,4,5,8-tetramethyl-6-(1-ethyl-5-ethanesulfonyloxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound Ic-2).

後処理

  1. customto react at room temperature for 2 hours
  2. temperaturefurther refluxed
  3. temperatureunder heat for 2 hours
  4. temperatureto cool
  5. customa methylene chloride layer was recovered
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resultant oil was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-b437e05b173c435b946ece88305eb18d
出典データセット
uspto-grants-1998_03
特許番号
US05723408

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