Triethylamine → 2-(3,4-Dichlorophenyl)-N-methoxy-N-methylacetamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	3,4-Dichlorophenylacetic acid	HCID 79874	—
Reactant	Methanamine, N-methoxy-, hydrochloride (1:1)	HCID 81138	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	HCID 178418300	HCID 178418300	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-(3,4-Dichlorophenyl)-N-methoxy-N-methylacetamide	HCID 15278933	72.7%

Reaction Steps

A mixture of 2-(3,4-dichlorophenyl)acetic acid (1 g, 4.9 mmol), N,O-dimethylhydroxylamine hydrochloride (480 mg, 4.9 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (940 mg, 4.9 mmol), hydroxybenzotriazole (660 mg, 4.9 mmol), and triethylamine (2.5 g, 25 mmol) in dichloromethane (30 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water (30 mL), and extracted with EtOAc (30 mL×3). The combined organic layers were dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (PE:EtOAc=10:1) to afford 2-(3,4-dichlorophenyl)-N-methoxy-N-methylacetamide (880 mg, yield 72.7%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09283229B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-ddbf2c0160154c92a82feef68b033402
Source note	uspto-grants-2016_03