Methyl iodide → HCID 59239867, compound

HRID 1668375Notes

Reaction equation

HRID 1668375 reaction equation
[C:1]([NH:4][N:5]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15][CH:14]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2].[CH3:24]I.[H-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:1]([N:4]([CH3:24])[N:5]([C:13]1[CH:14]=[CH:15][C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:18]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59239858HCID 59239858, compound

Product 1

HCID 59239867HCID 59239867, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-acetyl-1-[4-(ethoxycarbonyl)phenyl]hydrazinecarboxylate (606 mg) was dissolved in DMF (10 ml), and methyl iodide (0.14 ml) and then sodium hydride (60%, 83 mg) were added at 0° C. The mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with ethyl acetate, and washed with water and then saturated brine. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 (volume ratio)→1:1 (volume ratio)), and further recrystallized from ethyl acetate-hexane to give the title compound (608 mg) as colorless crystals.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane
  5. customethyl acetate=19:1 (volume ratio)→1:1 (volume ratio)), and further recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7823687a4cae432a821201126569e5c9
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

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