Diethylamine → N,N-diethyl-3-methoxybenzamide

Participants

Role	Name	HCID	Charge
Reactant	Diethylamine	HCID 8021	—
Reactant	3-Methoxybenzoic Acid	HCID 11461	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N,N-diethyl-3-methoxybenzamide	HCID 669438	—

Reaction Steps

To a solution of m-anisic acid (0.5 g; 3.29 mmol) and HATU (1.4 g; 3.68 mmol) in DMF (5 mL) was added N,N-diisopropylethylamine (2 mL; 11.48 mmol). The reaction was stirred at room temperature for 30 min. Diethylamine (0.377 mL; 3.62 mmol) was added to the reaction. The mixture was stirred at room temperature for 1.5 d, diluted with H2O (5 mL), and extracted with EtOAc (2×5 mL). The organic layer was dried over MgSO4 and concentrated to afford Compound 15a. The crude product was used in the next reaction without further purification. MS: m/z 208.2 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08685990B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-04d4ebe63e3d4e0f925de11bc81a33e7
Source note	uspto-grants-2014_04