N,N'-Dimethylethylenediamine → 1-(3-(Benzylthio)-2-methylphenyl)pyrrolidin-2-one

Participants

Role	Name	HCID	Charge
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Pyrrolidone	HCID 12025	—
Reactant	Benzyl(3-bromo-2-methylphenyl)sulfane	HCID 66911186	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Toluene	HCID 1140	—
Product	1-(3-(Benzylthio)-2-methylphenyl)pyrrolidin-2-one	HCID 66911127	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

Intermediate 83 (7 g, 23.87 mmol), pyrrolidin-2-one (4.06 g, 47.74 mmol), CuI (909 mg, 4.77 mmol), N,N′-dimethylethylene diamine (10.28 ml, 95.49 mmol) and K2CO3 (7.25 g, 52.52 mmol) were suspended in toluene (10 ml) under N2 and heated to 110° C. for 16 h. After cooling to RT the reaction mixture was quenched by the addition of 100 ml water and extracted with ethyl acetate (three times). The organic layers were combined and washed with water and sat. aq NaCl-solution, dried with Na2SO4, filtered and evaporated to dryness, and purified by silica gel chromatography.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08378092B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-9d5ab9fcdb5542cba0f96af3891d264f
Source note	uspto-grants-2013_02