Methyl iodide → HCID 19994968, compound

HRID 2248613Notes

Reaction equation

HRID 2248613 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([NH:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1)[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.[CH3:23]I.[H-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:10]1[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=1)[N:17]([CH3:23])[N:18]1[CH:22]=[N:21][CH:20]=[N:19]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19994951HCID 19994951, compound

Product 1

HCID 19994968HCID 19994968, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 40.0 g (0.119 mol) of N-[1-(2,4-dichlorophenyl)-1-(4-fluorophenyl)methyl]-1H-1,2,4-triazol-1-amine and 40 mL (0.64 mol) of methyl iodide in 250 mL dimethyl formamide was cooled to 0° C. Sodium hydride (4.5 g; 0.19 mol, freed from oils) was added portionwise. The reaction mixture was warmed to room temperature, stirred 1 h and quenched by dropwise addition of aqueous ammonium chloride. The mixture was diluted with ether, and washed three times with water and with brine. Drying (MgSO4) and removal of solvent gave product as an oil. Crystallization from hexanes afforded 27.7 g (66% yield) of the desired product as a white solid; mp 118°-119° C.

Workup

  1. customquenched by dropwise addition of aqueous ammonium chloride
  2. additionThe mixture was diluted with ether
  3. washwashed three times with water
  4. customDrying
  5. custom(MgSO4) and removal of solvent
  6. customgave product as an oil
  7. customCrystallization from hexanes

Sources & evidence

ORD record
ord-c83b1370ac2f411e9cc752785dc3bc81
Source dataset
uspto-grants-1991_08
Patent number
US05041458

Reaction notes

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