Dimethylformamide → HCID 86681578, compound

HRID 339432Notes

Reaction equation

HRID 339432 reaction equation
IC.[CH3:3]N(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH:14]([O:17][NH:18][C:19](=[O:31])[C:20](=[N:26][O:27][CH:28]([CH3:30])[CH3:29])[N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)([CH3:16])[CH3:15]>O>[CH:28]([O:27][N:26]=[C:20]([N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)[C:19](=[N:18][O:17][CH:14]([CH3:16])[CH3:15])[O:31][CH3:3])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86681579HCID 86681579, compound

Product 1

HCID 86681578HCID 86681578, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.22 g (1.55 mmol) of iodomethane was added, with ice-cooling, to 5 ml of an N,N-dimethylformamide solution containing 0.22 g (1.59 mmol) of potassium carbonate and 0.4 g (1.57 mmol) of the N-isopropoxy-2-isopropoxyimino-2-(1H-1,2,4-triazol-1-yl)acetamide produced in Example 8, followed by stirring at room temperature for 20 hours. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The extract solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (elutant:ethyl acetate/hexane=1/2) to obtain 0.12 g (yield: 29%) of a title compound.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract solution was washed with an aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elutant:ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-22fb7dd3fd5c4d65ad72574dfe7708bd
Source dataset
uspto-grants-2014_11
Patent number
US08895035B2

Reaction notes

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