Water → 4-[Ethyl(methyl)amino]benzaldehyde

HRID 1663604Notes

Reaction equation

HRID 1663604 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][NH:11][CH2:12][CH3:13].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH2:12]([N:11]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH3:10])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12219N-MethylethylamineHCID 680234-Fluorobenzaldehyde

Product 1

HCID 133962824-[Ethyl(methyl)amino]benzaldehydeYield 89%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-fluorobenzaldehyde (1.5 g) and methylethylamine (1.56 mL) in dimethylsulfoxide (9 mL) was added potassium carbonate (2.17 g) and the mixture was stirred by using a microwave synthesizer (Biotage LTD.) at 120° C. for 2 hours. Thereto was added water and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated in vacuo. The resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=95:5→80:20) to give 4-(N-ethyl-N-methylamino)benzaldehyde (1.89 g, yield: 89%).

Workup

  1. customat 120° C.
  2. customfor 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=95:5→80:20)

Sources & evidence

ORD record
ord-5ed1b6e0df1f4b21b7ae5f6f131b099c
Source dataset
uspto-grants-2011_10
Patent number
US08034949B2

Reaction notes

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