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

HRID 854138ノート

反応式

HRID 854138 の反応式
Br.[F:2][CH:3]([F:20])[O:4][C:5]1[N:9]([CH3:10])[N:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[C:6]=1[CH2:15][S:16][C:17](=N)[NH2:18].C(=O)([O-])[O-].[K+].[K+].O.C(S(C1[CH2:37][C:36]([CH3:39])([CH3:38])[O:35]N=1)(=O)=O)C>C(O)C.CN(C)C=O>[F:2][CH:3]([F:20])[O:4][C:5]1[N:9]([CH3:10])[N:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[C:6]=1[CH2:15][S:16][C:17]1[CH2:37][C:36]([CH3:39])([CH3:38])[O:35][N:18]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium Carbonate2 回HCID 178629235,5-Dimethyl-3-ethylsulfonyl-2-isoxazolineHCID 230756895-(Difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl-carbamimidothioic acid methyl ester hydrobromide

生成物 1

HCID 116174263-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline収率 86.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1.93 g (5.00 mmol) of 2-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethyl)-isothiourea hydrobromide in 10 ml of ethanol were added 0.83 g (6.00 mmol) of anhydrous potassium carbonate and 5 ml of water, followed by 30 minutes of stirring at room temperature. Thereto were added a solution of 0.95 g (5.00 mmol) of 3-ethanesulfonyl-5,5-dimethyl-2-isoxazoline in 5 ml of N,N-dimethylformamide and 0.83 g (6.00 mmol) of anhydrous potassium carbonate at room temperature, followed by further 3 hours of stirring at 50° C. After the completion of the reaction was confirmed, the solvent was removed by evaporation under reduced pressure. The obtained residue was poured into water and extracted with ethyl acetate. The resulting organic layer was washed with water 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 1.55 g (yield: 86.1%) of 3-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline.

後処理

  1. waitfollowed by further 3 hours
  2. stirringof stirring at 50° C
  3. customthe solvent was removed by evaporation under reduced pressure
  4. additionThe obtained residue was poured into water
  5. extractionextracted with ethyl acetate
  6. washThe resulting organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed by evaporation under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-a05930442e31439e8958e306809753e6
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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