Potassium Carbonate → 1-[4-chloro-5-(4-cyanophenoxy)-2-fluorophenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one

HRID 1090987노트

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HRID 1090987 반응식
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:13](=[O:14])[N:12]([CH:15]([F:17])[F:16])[C:11]([CH3:18])=[N:10]2)=[C:4]([F:19])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].F[C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=1>CN(C)C=O>[Cl:1][C:2]1[C:7]([O:8][C:27]2[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=2)=[CH:6][C:5]([N:9]2[C:13](=[O:14])[N:12]([CH:15]([F:16])[F:17])[C:11]([CH3:18])=[N:10]2)=[C:4]([F:19])[CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 137694562-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

생성물 1

HCID 199122151-[4-chloro-5-(4-cyanophenoxy)-2-fluorophenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one수율 65.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

To a stirred solution of 5.0 g (0.017 mole) of 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one in 150 mL of N,N-dimethylformamide was added 2.8 g (0.020 mole) of potassium carbonate. The resultant mixture was stirred for ten minutes, and 2.1 g (0.017 mole) of 4-fluorobenzonitrile was added. The mixture was stirred and heated at 120° C. for approximately 18 hours. The solvent was removed from the mixture by distillation under reduced pressure leaving a residue which was partitioned between diethyl ether and water. The organic phase was separated, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure to give 4.4 g of 1-[4-chloro-5-(4-cyanophenoxy)-2-fluorophenyl]-4-difluoromethyl -4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one as a solid.

후처리

  1. customThe solvent was removed from the mixture by distillation under reduced pressure
  2. customleaving a residue which
  3. customwas partitioned between diethyl ether and water
  4. customThe organic phase was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-aec1f7f720484c8bb866d110ebb450e5
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05084085

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