Dimethylamine → 2-benzyloxyimino-3-methoxyimino-N,N-dimethylbutyramide

HRID 1069200Notes

Reaction equation

[CH2:1]([O:8][N:9]=[C:10]([C:14](=[N:16][O:17][CH3:18])[CH3:15])[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:23][NH:24][CH3:25].O>C1(C)C=CC=CC=1.CN(C)C=O>[CH2:1]([O:8][N:9]=[C:10]([C:14](=[N:16][O:17][CH3:18])[CH3:15])[C:11]([N:24]([CH3:25])[CH3:23])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 0.9 g (3.6 mmol) of 2-benzyloxyimino-3-methoxyiminobutyric acid in 15 ml of toluene, 0.5 g (4.0 mmol) of thionyl chloride and one drop of N,N-dimethylformamide were added and the mixture was stirred for 1 hour at 60° C. After cooling with an ice, 5 ml of 50% dimethylamine solution was added and the mixture was stirred for 0.5 hour at room temperature. 30 ml of water was added and the mixture was extracted three times with 50 ml of diethylether. After washing with water and a saturated aqueous sodium chloride, the organic layer was dried over with anhydrous magnesium sulfate and the solvent was distilled off to obtain a residue, which was then purified by a column chromatography on a silica gel (n-hexane/ethyl acetate) to obtain 0.53 g (yield: 53%) of 2-benzyloxyimino-3-methoxyimino-N,N-dimethylbutyramide as a colorless oil.

Workup

additionwas added
stirringthe mixture was stirred for 0.5 hour at room temperature
extractionthe mixture was extracted three times with 50 ml of diethylether
washAfter washing with water
dry with materiala saturated aqueous sodium chloride, the organic layer was dried over with anhydrous magnesium sulfate
distillationthe solvent was distilled off
customto obtain a residue, which
customwas then purified by a column chromatography on a silica gel (n-hexane/ethyl acetate)

Sources & evidence

ORD record: ord-abcb2cf2e4eb4c2494d9495d70b33a08
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06251949B1

Reaction notes

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