Dimethylamine → HCID 18763867, compound

HRID 1854652Notes

Reaction equation

HRID 1854652 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].[CH3:18][NH:19][CH3:20].C(O)C>CS(C)=O.O.C(OCC)(=O)C>[CH3:18][N:19]([CH3:20])[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 702EthanolHCID 11430Potassium CarbonateHCID 27373584-Fluoro-3-methoxybenzaldehyde

Product 1

HCID 18763867HCID 18763867, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

4-Fluoro-3-methoxybenzaldehyde (500 mg, 3.24 mmol) was dissolved in 6.9 mL of DMSO and 2.8 mL of water, and then potassium carbonate (0.45 g, 3.3 mmol) and dimethylamine solution in ethanol (0.88 mL, 5.5 M, 4.8 mmol) were added to the solution at room temperature, successively. After being stirred at 100° C. for 5 h, the reaction mixture was cooled to room temperature. The reaction mixture was diluted with ethyl acetate, and the solution was washed with water, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (eluting with hexane/ethyl acetate=4/1 to 2/1) to obtain the title compound as a pale yellow oil (569 mg, 98%).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. washthe solution was washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (eluting with hexane/ethyl acetate=4/1 to 2/1)

Sources & evidence

ORD record
ord-763de09bb3ad4654b5fa19fb4fcc7db3
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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