Dimethylformamide → 2-((dimethylamino)methylene)-N-(2-methylphenyl)-3-oxobutanamide

HRID 1526289Notes

Reaction equation

HRID 1526289 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[CH2:10][C:11](=[O:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].[CH3:21][N:22]([CH3:25])[CH:23]=O.COC(OC)N(C)C>O>[CH3:21][N:22]([CH:25]=[C:10]([C:11](=[O:13])[CH3:12])[C:9]([NH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])=[O:14])[CH3:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 71542'-MethylacetoacetanilideHCID 11430Potassium CarbonateHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 743979722-((dimethylamino)methylene)-N-(2-methylphenyl)-3-oxobutanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of N-(2-methylphenyl)-3-oxobutanamide (10.0 g), potassium carbonate (7.23 g) and N,N-dimethylformamide (130 mL) was added dropwise 1,1-dimethoxy-N,N-dimethylmethanamine (12.5 g) over 30 min at room temperature, and the reaction mixture was stirred at room temperature for 2 hr. The reaction mixture was slowly poured into water, and the mixture was extracted with dichloromethane. The extract was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (10.2 g).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-423b8b9b926a4ed7bcfb3e0a69db0862
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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