N,N-Dimethylaniline → HCID 59868739, compound

HRID 383715Notes

Reaction equation

HRID 383715 reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[N:12]=[C:11]([CH3:13])[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:9]([CH3:19])[N:8]=1.CN(C)C1C=CC=CC=1.C([O-])(O)=O.[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C>[Cl:3][C:7]1[N:12]=[C:11]([CH3:13])[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:9]([CH3:19])[N:8]=1

Participants

7

Reactant 4

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178469253HCID 178469253, compound

Product 1

HCID 59868739HCID 59868739, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

Phosphorus oxychloride (2.8 ml, 30 mmol) was added to a mixture of 6a (1.47 g, 7.5 mmol), benzyltriethylammonium chloride (1.71 g, 7.5 mmol) and N,N-dimethylaniline (1.82 g, 15 mmol) in acetonitrile (30 ml). The mixture was reflux for 5 hours. The mixture was poured into ice water and neutralized with NaHCO3. The solution was extracted with ethyl acetate. The organic layer washed with brine, dried over MgSO4, concentrated and chromatographed to obtain 6b, (1.02 g, 4.75 mmol, 63%).

Workup

  1. temperatureThe mixture was reflux for 5 hours
  2. extractionThe solution was extracted with ethyl acetate
  3. washThe organic layer washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customchromatographed

Sources & evidence

ORD record
ord-b1d878878a3d4ef9a52f59ebc1fd89e1
Source dataset
uspto-grants-2013_02
Patent number
US08367684B2

Reaction notes

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