p-Fluoronitrobenzene → 1-[2-Fluoro-4-chloro-5-(4-nitrophenoxy)phenyl]-3-methyl-4-(difluoromethyl)-1H-1,2,4-triazol-5(4H)-one

HRID 1090978노트

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HRID 1090978 반응식
[H-].[Na+].[Cl:3][C:4]1[C:9]([OH:10])=[CH:8][C:7]([N:11]2[C:15](=[O:16])[N:14]([CH:17]([F:19])[F:18])[C:13]([CH3:20])=[N:12]2)=[C:6]([F:21])[CH:5]=1.F[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1>CN(C)C=O>[Cl:3][C:4]1[C:9]([O:10][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[CH:8][C:7]([N:11]2[C:15](=[O:16])[N:14]([CH:17]([F:18])[F:19])[C:13]([CH3:20])=[N:12]2)=[C:6]([F:21])[CH:5]=1

참가 물질

5

반응물 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 137694562-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

생성물 1

HCID 199122141-[2-Fluoro-4-chloro-5-(4-nitrophenoxy)phenyl]-3-methyl-4-(difluoromethyl)-1H-1,2,4-triazol-5(4H)-one수율 76.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
80 °C

실험 절차

To a stirred mixture of 0.91 g (0.019 mole) of sodium hydride in 30 mL of N,N-dimethylformamide was added slowly a solution of 5.50 g (0.019 mole) of 1-[4-chloro-2-fluoro-5-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one in 30 mL of N,N-dimethylformamide. To this mixture was added 2.68 g (0.019 mole) of 4-fluoronitrobenzene. The resultant mixture was stirred at room temperature for approximately 18 hours and then was heated at 80° C. for one hour. The mixture was allowed to cool and was poured into ice water. The aqueous mixture was extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 6.0 g of 1-[4-chloro-2-fluoro-5-(4-nitrophenoxy)phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one as a solid, m.p. 115°-117° C., Compound 4 of Table 1.

후처리

  1. temperatureto cool
  2. extractionThe aqueous mixture was extracted with diethyl ether
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-c471222f7957415e95444bca2f648932
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05084085

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