Triethylamine → 5-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	2-Methoxy-N-methylaniline	HCID 2759579	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	5-Bromo-4-chloro-2-hydroxybenzoic acid	HCID 11021353	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	5-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide	HCID 68602584	10.1%

Reaction Steps

To a stirring dichloromethane (40 mL) solution containing 5-bromo-4-chloro-2-hydroxybenzoic acid (2.0 g, 8.0 mmol), were added triethylamine (2.2 mL, 16.0 mmol), HATU (4.5 g, 12 mmol) and 2-methoxyl-N-methylaniline (1.19 g, 8.7 mmol). The mixture was stirred at rt for 16 hrs and water was added. The organic layer was separated, washed with NaHCO3, dried over Na2SO4, filtered and concentrated. The residue was purified via silica gel flash column chromatography eluting with 20% ethyl acetate in hexane to afford 5-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide (300 mg). MS [M+H]+: 371.9; tR=2.60 min (method 1)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08952161B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-7527aa1243974cc9ad606317e40e8854
Source note	uspto-grants-2015_02