Hydrochloric Acid → HCID 22624532, compound

HRID 1636680Notes

Reaction equation

HRID 1636680 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[F:11][C:12]([F:30])([CH:27]([F:29])[F:28])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH:25]=[N:24][NH:23][C:22]2=[O:26])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C(OCC)(=O)C.O.CN(C)C=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:23]2[C:22](=[O:26])[N:21]([C:18]3[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:12]([F:11])([F:30])[CH:27]([F:28])[F:29])=[CH:20][CH:19]=3)[CH:25]=[N:24]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 10779907HCID 10779907, compound

Product 1

HCID 22624532HCID 22624532, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-fluoronitrobenzene (3.1 g), 4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (5.8 g), potassium carbonate (13.8 g) and N,N-dimethylformamide (60 ml) was stirred at 80° C. for 2 hours. The resultant was cooled and poured into water (500 ml). The mixture was neutralized with hydrochloric acid and the precipitated crystals were collected by filtration. The crystals thus obtained were dissolved in ethyl acetate (300 ml) and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was crystallized from a mixture of ethyl acetate and diisopropyl ether to give 2-(4-nitrophenyl)-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (5.5 g, 67%) as yellow crystalline powders.

Workup

  1. temperatureThe resultant was cooled
  2. filtrationthe precipitated crystals were collected by filtration
  3. customThe crystals thus obtained
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was crystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-402c1063b8d34515857c399292f9fa4b
Source dataset
uspto-grants-2000_03
Patent number
US06034248

Reaction notes

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