Potassium Carbonate → HCID 19912233, compound

HRID 1090992Notes

Reaction equation

HRID 1090992 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[N:13]([CH:16]([F:18])[F:17])[C:12]([CH3:19])=[N:11]1.C(=O)([O-])[O-].[K+].[K+].[Cl:26][C:27]1[CH:28]=[C:29]([N+:34]([O-:36])=[O:35])[CH:30]=[CH:31][C:32]=1F>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][C:32]2[CH:31]=[CH:30][C:29]([N+:34]([O-:36])=[O:35])=[CH:28][C:27]=2[Cl:26])=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[N:13]([CH:16]([F:17])[F:18])[C:12]([CH3:19])=[N:11]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 13253747HCID 13253747, compound

Product 1

HCID 19912233HCID 19912233, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.0 g (0.032 mole) of 1-(2,4-dichloro-5-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro -3-methyl-1,2,4-triazol-5(1H)-one, 5.52 g (0.040 mole) of potassium carbonate, and 7.02 g (0.040 mole) of 3-chloro-4-fluoronitrobenzene in 60 ml of N,N-dimethylformamide was stirred at room temperature for approximately 18 hours. The reaction mixture was poured into ice-water. This aqueous mixture was extracted with diethyl ether. The extract :;as dried over anhydrous magnesium sulfate and was filtered. The filtrate was evaporated under reduced pressure leaving a residue. This residue was purified by column chromatography on silica gel to yield 10.4 g of 1-[2,4-dichloro-5-(2-chloro-4-nitrophenoxy)phenyl]-4-difluoromethyl -4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one as a solid, m.p. 135°-135.5° C., compound 179 of Table 1.

Workup

  1. extractionThis aqueous mixture was extracted with diethyl ether
  2. extractionThe extract
  3. dry with material;as dried over anhydrous magnesium sulfate
  4. filtrationwas filtered
  5. customThe filtrate was evaporated under reduced pressure
  6. customleaving a residue
  7. customThis residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3da48ebe07b34e6e99a1279d6ea23d5e
Source dataset
uspto-grants-1992_01
Patent number
US05084085

Reaction notes

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