Methyl iodide → HCID 68469900, compound

HRID 502994Notes

Reaction equation

HRID 502994 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]([CH3:27])[C:12]([C:15]([NH:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([CH3:17])[CH3:16])=[N:13][N:14]=1.CI.[C:30](=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.CN(C=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]([CH3:27])[C:12]([C:15]([N:18]([CH3:30])[C:19](=[O:26])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([CH3:17])[CH3:16])=[N:13][N:14]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 68470234HCID 68470234, compound

Product 1

HCID 68469900HCID 68469900, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, 16 mg) was added to a DMF (10 ml) solution of N-{1-[5-(2-chlorophenyl)-4-methyl-4H-1,2,4-triazol-3-yl]-1-methylethyl}benzamide (130 mg), followed by stirring at room temperature for 30 minutes. Then, methyl iodide (0.027 ml) was added thereto and the whole was stirred at room temperature for 1 hour. A saturated aqueous sodium hydrogen carbonate solution and chloroform were added to the reaction solution and then the organic layer was separated. Furthermore, the organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting crude product was purified by flash column chromatography (chloroform:methanol=100:3) to obtain 104 mg of N-{1-[5-(2-chlorophenyl)-4-methyl-4H-1,2,4-triazol-3-yl]-1-methylethyl}-N-methylbenzamide (colorless solid).

Workup

  1. stirringthe whole was stirred at room temperature for 1 hour
  2. customthe organic layer was separated
  3. washFurthermore, the organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed by evaporation under reduced pressure
  7. customThe resulting crude product was purified by flash column chromatography (chloroform:methanol=100:3)

Sources & evidence

ORD record
ord-e4dd630910324f9d8019a594c8619f61
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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