N,N-Dimethylaniline → HCID 59868739, compound

Participants

Role	Name	HCID	Charge
Reactant	N,N-Dimethylaniline	HCID 949	—
Reactant	Phosphorus oxychloride	HCID 24813	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	HCID 178469253	HCID 178469253	—
Catalyst	Benzyl triethylammonium chloride	HCID 66133	—
Solvent	Acetonitrile	HCID 6342	—
Product	HCID 59868739	HCID 59868739	63.3%

Reaction Steps

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%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08367684B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-b1d878878a3d4ef9a52f59ebc1fd89e1
Source note	uspto-grants-2013_02