Potassium Carbonate → 3-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline

HRID 854136ノート

反応式

HRID 854136 の反応式
[CH2:1]([S:3]([C:6]1[CH2:10][C:9]([CH3:12])([CH3:11])[O:8][N:7]=1)(=O)=O)[CH3:2].[SH-].[Na+].C(=O)([O-])[O-].[K+].[K+].BrCC1[C:24]([C:33]([F:36])([F:35])[F:34])=[N:25][N:26]([CH3:32])[C:27]=1[O:28][CH:29]([F:31])[F:30]>CN(C)C=O.O>[F:31][CH:29]([F:30])[O:28][C:27]1[N:26]([CH3:32])[N:25]=[C:24]([C:33]([F:34])([F:35])[F:36])[C:2]=1[CH2:1][S:3][C:6]1[CH2:10][C:9]([CH3:12])([CH3:11])[O:8][N:7]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 28015Sodium hydrosulfideHCID 117228384-(bromomethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazoleHCID 178629235,5-Dimethyl-3-ethylsulfonyl-2-isoxazoline

生成物 1

HCID 116174263-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline収率 58%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6.7 g (35.0 mmol) of 3-ethanesulfonyl-5,5-dimethyl-2-isoxazoline in 50 ml of N,N-dimethylformamide was added 5.6 g (purity: 70%, 70.0 mmol) of sodium hydrosulfide, followed by 1 hour of stirring at room temperature. Thereafter, 4.8 g (35.0 mmol) of potassium carbonate and 10.8 g (35.0 mmol) of 4-bromomethyl-5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole were added thereto, followed by stirring at room temperature overnight. After the completion of the reaction was confirmed, the reaction solution was poured into water and extracted with ethyl acetate. The resulting organic layer was washed with water and saline and then dried over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure and the residue was purified by silica gel column chromatography to obtain 7.3 g (yield: 57.9%) of 3-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline as white crystals (melting point: 39 to 40° C.).

後処理

  1. stirringby stirring at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe resulting organic layer was washed with water and saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by evaporation under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-e4b32ddd01954ddb871abe5de2bf8a8e
出典データセット
uspto-grants-2007_08
特許番号
US07256298B2

反応ノート

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