Dimethylformamide → HCID 131733167, compound

HRID 1526344Notes

Reaction equation

HRID 1526344 reaction equation
[Cl: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>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[C:10](=[CH:21][N:22]([CH3:25])[CH3:23])[C:11](=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7156Acetoacetyl-2-chloroanilideHCID 11430Potassium CarbonateHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 131733167HCID 131733167, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of N-(2-chlorophenyl)-3-oxobutanamide (2.63 g), potassium carbonate (1.72 g) and N,N-dimethylformamide (31.0 mL) was added dropwise 1,1-dimethoxy-N,N-dimethylmethanamine (3.30 mL) 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 (2.30 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-bdea009a67de40bc86cc328dc0f09599
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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