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

HRID 854138노트

반응식

HRID 854138 반응식
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

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium Carbonate2회HCID 178629235,5-Dimethyl-3-ethylsulfonyl-2-isoxazolineHCID 230756895-(Difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl-carbamimidothioic acid methyl ester hydrobromide

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a05930442e31439e8958e306809753e6
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07256298B2

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