Hydrochloric Acid → 1-[2,4-dichloro-5-(4-nitrophenoxy)phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one

HRID 1090991Notes

Reaction equation

HRID 1090991 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[C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1.Cl>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 74741-Chloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 13253747HCID 13253747, compound

Product 1

HCID 199122081-[2,4-dichloro-5-(4-nitrophenoxy)phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-oneYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A stirred mixture of 1.0 g (0.0032 mole) of 1-(2,4-dichloro-5-hydroxyphenyl)-4-difluoromethyl -4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one, 0.66 g (0.0048 mole) of potassium carbonate, and 0.76 g (0.0048 mole) of 4-chloronitrobenzene in 20 ml of N,N-dimethylformamide was heated at 120° C. for approximately 18 hours. The reaction mixture was cooled and was poured into ice-water. This aqueous mixture was neutralized with hydrochloric acid and then was extracted with ethyl acetate. The organic phase was washed with water and then was dried over anhydrous magnesium sulfate. This mixture was filtered, and the filtrate was evaporated under reduced pressure leaving an orange oil. The orange oil was purified by column chromatography on silica gel, eluting with methylene chloride to yield 1.2 g of 1-[2,4-dichloro-5-(4-nitrophenoxy)phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one as a solid, m.p. 99°-101° C., compound 92 of Table 1.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionwas extracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationThis mixture was filtered
  6. customthe filtrate was evaporated under reduced pressure
  7. customleaving an orange oil
  8. customThe orange oil was purified by column chromatography on silica gel
  9. washeluting with methylene chloride

Sources & evidence

ORD record
ord-dc500a947d0f41e0816a3de2f62eea6d
Source dataset
uspto-grants-1992_01
Patent number
US05084085

Reaction notes

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