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

HRID 1090978ノート

反応式

HRID 1090978 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c471222f7957415e95444bca2f648932
出典データセット
uspto-grants-1992_01
特許番号
US05084085

反応ノート

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