Methyl iodide → HCID 68780962, compound

HRID 2263047Notes

Reaction equation

HRID 2263047 reaction equation
[C:1]1([C:7]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([NH:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)=[O:19])[CH2:14][CH2:13]3)[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:29]I.[Cl-].[NH4+]>CN(C)C=O>[CH3:29][N:20]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[C:18]([N:15]1[CH2:16][CH2:17][N:12]([C:10]2[S:9][N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:11]=2)[CH2:13][CH2:14]1)=[O:19]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11552354HCID 11552354, compound

Product 1

HCID 68780962HCID 68780962, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen gas stream, to a solution of 4-(3-phenyl-1,2,4-thiadiazol-5-yl)-N-pyridin-3-ylpiperazine-1-carboxamide (100 mg, 0.273 mmol) in dimethylformamide (1.0 ml) was added, under ice-cooling, sodium hydride (13.1 mg, 0.327 mmol), and the mixture was stirred at room temperature for 30 minutes. Methyl iodide (0.020 ml, 0.327 mmol) was added thereto under ice-cooling, and the mixture was stirred at 0° C. for 30 minutes, followed by stirring at room temperature for 2 hours and half. An aqueous saturated ammonium chloride solution was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from a mixed solvent of hexane and ethyl acetate to give 43.0 mg (41.4%) of the desired product as a solid.

Workup

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. stirringby stirring at room temperature for 2 hours
  4. extractionthe resulting solution was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  9. customrecrystallized from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-faedab861bbf4bbdb58b73a1f6c4d198
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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