Methyl iodide → HCID 14853659, compound

HRID 2073690Notes

Reaction equation

HRID 2073690 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][CH:12]([CH3:14])[CH3:13])=[CH:6][C:5]=1[N:15]1[C:19](=[O:20])[NH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[N:16]1.I[CH3:26]>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][CH:12]([CH3:14])[CH3:13])=[CH:6][C:5]=1[N:15]1[C:19](=[O:20])[N:18]([CH3:26])[C:17]([C:21]([F:22])([F:23])[F:24])=[N:16]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1361615961-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-trifluoromethyl-4,5-dihydro-1,2,4-triazol-5(1H)-one

Product 1

HCID 14853659HCID 14853659, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a dry nitrogen atmosphere 0.1 g (0.0038 mole) of dry sodium hydride was added to a stirred solution of 1.3 g (0.0035 mole) of 1-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-trifluoromethyl-4,5-dihydro-1,2,4-triazol-5(1H)-one in 30 mL of N,N-dimethylformamide. The mixture was stirred at room temperature for 20 minutes and 0.6 g (0.0038 mole) of iodomethane was added. After complete addition the mixture was warmed to 65° C. and stirred at that temperature for one hour. The mixture was allowed to cool to room temperature and stir for approximately 18 hours. Most of the solvent was removed by distillation under reduced pressure to leave a liquid residue. This residue was partitioned between water and diethyl ether. The organic phase was washed first with a 2N sodium hydroxide solution followed by water. The organic solution was dried over an anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 1.2 g of 1-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-trifluoromethyl-4,5-dihydro-4-methyl-1,2,4-triazol-5(1H)-one as a solid (mp 96°-98° C.), Compound 35.

Workup

  1. additionAfter complete addition the mixture
  2. temperaturewas warmed to 65° C.
  3. stirringstirred at that temperature for one hour
  4. temperatureto cool to room temperature
  5. stirringstir for approximately 18 hours
  6. customMost of the solvent was removed by distillation under reduced pressure
  7. customto leave a liquid residue
  8. customThis residue was partitioned between water and diethyl ether
  9. washThe organic phase was washed first with a 2N sodium hydroxide solution
  10. dry with materialThe organic solution was dried over an anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-35380395ca6a4e5c9f18525bdf219397
Source dataset
uspto-grants-1990_04
Patent number
US04919708

Reaction notes

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