Hydrochloric Acid → N,N-Diethyl-p-toluamide

HRID 1454274Notes

Reaction equation

HRID 1454274 reaction equation
CNC.[N:4]1[CH:9]=[CH:8]C=[CH:6][CH:5]=1.[C:10]1([CH3:17])[CH:15]=[CH:14]C(Cl)=[CH:12][CH:11]=1.Cl.CCCCCC.C([O:28][CH2:29][CH3:30])(=O)C>C(Cl)Cl>[CH2:5]([N:4]([CH2:9][CH3:8])[C:29](=[O:28])[C:30]1[CH:12]=[CH:11][C:10]([CH3:17])=[CH:15][CH:14]=1)[CH3:6]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 1049PyridineHCID 78104-ChlorotolueneHCID 21226206Ethyl acetate hexane

Product 1

HCID 75946N,N-Diethyl-p-toluamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dimethyl amine (13.00 g, 177.87 mmol, 18.40 mL) and pyridine (38.37 g, 485.10 mmol, 39.23 mL) were dissolved in 500 mL of anhydrous DCM under argon and cooled to 0EC. p-Tolyl chloride (25.00 g, 161.70 mmol), dissolved in 75 mL of anhydrous DCM, was added to the solution slowly. On completion of addition the solution was slowly warmed to room temp and stirred for 12 h. The reaction mixture was poured into 1N HCl and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate, water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (4:1 hexane/ethyl acetate) Yield 25.36 g.

Workup

  1. temperaturecooled to 0EC
  2. additionwas added to the solution slowly
  3. additionOn completion of addition the solution
  4. extractionthe aqueous layer was extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with saturated sodium bicarbonate, water, brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe solution was filtered
  8. customthe solvent removed under reduced pressure
  9. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-85401510f32f4aa793b43ea935fbdfba
Source dataset
uspto-grants-2009_01
Patent number
US07479495B2

Reaction notes

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