N-methyl-N-phenyl-hydrazine → HCID 54029323, compound

HRID 1069194Notes

Reaction equation

HRID 1069194 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:10]([CH3:12])=O)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6].[CH3:13][N:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH2:15]>C(O)C.C(O)(=O)C>[CH3:1][O:2][N:3]=[C:4]([C:10](=[N:15][N:14]([CH3:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:12])[C:5]([N:7]([CH3:9])[CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 36299N-methyl-N-phenyl-hydrazineHCID 54128125HCID 54128125, compound

Product 1

HCID 54029323HCID 54029323, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

1.0 g (5.8 mmol) of 2-methoxyimino-N,N-dimethylacetoacetamide was dissolved in 15 ml of ethanol and 0.5 ml of acetic acid, and 0.78 g (6.4 mmol) of N-methyl-N-phenylhydrazine was added and the mixture was stirred for 24 hours at room temperature. After distilling the solvent off, water was added and the mixture was extracted three times with 20 ml of diethylether. After washing with a dilute hydrochloric acid, water and a saturated aqueous sodium chloride, the mixture was dried over with anhydrous magnesium sulfate, and the solvent was distilled off, and finally the residue thus obtained was purified by a column chromatography on a silica gel (n-hexane/ethyl acetate) to obtain 1.38 g (yield: 86%) of 2-methoxyimino-N,N-dimethy-3-(N-methyl-N-phenylhydrazono)butyramide as a yellow oil. 1H-NMR(CDCl3) δ ppm:2.13(3H, s), 2.90(3H,s), 3.07(3H, s), 3.29(3H, s), 3.99(3H,s), 6.90-7.02(3H, m), 7.33-7.29(2H, m).

Workup

  1. distillationAfter distilling the solvent off, water
  2. additionwas added
  3. extractionthe mixture was extracted three times with 20 ml of diethylether
  4. washAfter washing with a dilute hydrochloric acid, water
  5. dry with materiala saturated aqueous sodium chloride, the mixture was dried over with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customfinally the residue thus obtained
  8. customwas purified by a column chromatography on a silica gel (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7101aedea083464c8a6ee9bc9cd6567b
Source dataset
uspto-grants-2001_06
Patent number
US06251949B1

Reaction notes

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