Chloroacetic Acid → 2-Chloro-N-(4-methoxyphenyl)acetamide

Participants

Role	Name	HCID	Charge
Reactant	Chloroacetic Acid	HCID 300	—
Reactant	P-Anisidine	HCID 7732	—
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-Chloro-N-(4-methoxyphenyl)acetamide	HCID 31123	20%

Reaction Conditions

Temperature	30 °C

Reaction Steps

A mixture of 4-methoxyaniline (5.00 g, 40.6 mmol), chloroacetic acid (8.6 g, 91.5 mmol), EDCI (12.0 g, 61.2 mmol), HOBT (8.4 g, 61.3 mmol) and NMM (13 mL, 122 mmol) in anhydrous CH2Cl2 (50 mL) was stirred at 30° C. for 3 hours. The mixture was quenched with ice water, and then extracted with CH2Cl2 (30 mL×2). The combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by silica gel column (PE/EtOAc=5/1) to give the product (1.60 g, yield 20%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09433618B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-b77fed58023540039334e25082c6416a
Source note	uspto-grants-2016_09