N,N'-Dimethylethylenediamine → Methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Oxazolidinone	HCID 73949	—
Reactant	Methyl 3-bromo-5-iodobenzoate	HCID 21942573	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Acetonitrile	HCID 6342	—
Product	Methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoate	HCID 67229228	80%

Reaction Conditions

Temperature	90 °C

Reaction Steps

A suspension of 3-bromo-5-iodo-benzoic acid methyl ester (682 mg, 2 mmol), oxazolidin-2-one (191 mg, 2.2 mmol), CuI (76 mg, 0.4 mmol), potassium carbonate (545 mg, 4 mmol) and N,N′-dimethyl-ethane-1,2-diamine (86 uL, 0.8 mmol) in acetonitrile (15 mL) was stirred for 16 hours at 90° C. The precipitate was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford 3-bromo-5-(2-oxo-oxazolidin-3-yl)-benzoic acid methyl ester (480 mg, 80%) which was used for next step without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08354443B2
Source dataset	uspto-grants-2013_01
ORD ID	ord-76d820331c864ce989db863d5708d70c
Source note	uspto-grants-2013_01