Methyl iodide → 1-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-difluoromethyl-4,5-dihydro-4-methyl-1,2,4-triazol-5(1H)-one

HRID 1382155Notes

Reaction equation

HRID 1382155 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[NH:16][C:15]([CH:19]([F:21])[F:20])=[N:14]1.[C:22](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[N:16]([CH3:22])[C:15]([CH:19]([F:20])[F:21])=[N:14]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1357451031-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-difluoromethyl-4,5-dihydro-1,2,4-triazol-5(1H)-one

Product 1

HCID 143924861-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-difluoromethyl-4,5-dihydro-4-methyl-1,2,4-triazol-5(1H)-oneYield 61.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A stirred mixture of 4.0 g (0.012 mole) of 1-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-difluoromethyl-4,5-dihydro-1,2,4-triazol-5(1H)-one and 4.1 g (0.03 mole) of potassium carbonate in 160 mL of acetone was heated at reflux for 0.5 hours then cooled to about 50° C. Methyl iodide, 8.4 g (0.06 mole), was added and the mixture stirred at 45° for one hour then at reflux for one hour. The mixture was cooled to room temperature and evaporated under reduced pressure to leave an oil. This oil was partitioned between methylene chloride and water. The organic phase was washed with a 10% aqueous sodium hydroxide solution and then dried over anhydrous magnesium sulfate. The mixture was filtered and the filtrate evaporated under reduced pressure to leave an oil. This oil solidified when stirred with petroleum ether and upon filtration provided 2.6 g of 1-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-difluoromethyl-4,5-dihydro-4-methyl-1,2,4 -triazol-5-(1H)-one (mp 95°-97° C).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 0.5 hours
  3. temperatureat reflux for one hour
  4. temperatureThe mixture was cooled to room temperature
  5. customevaporated under reduced pressure
  6. customto leave an oil
  7. customThis oil was partitioned between methylene chloride and water
  8. washThe organic phase was washed with a 10% aqueous sodium hydroxide solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThe mixture was filtered
  11. customthe filtrate evaporated under reduced pressure
  12. customto leave an oil

Sources & evidence

ORD record
ord-100b7c3c3cc648009f70b9f2f08aec05
Source dataset
uspto-grants-1989_02
Patent number
US04806145

Reaction notes

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