N,N'-Dimethylethylenediamine → 4-(3-(Benzylthio)-2-ethylphenyl)morpholin-3-one

Participants

Role	Name	HCID	Charge
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	3-Morpholinone	HCID 66953	—
Reactant	Benzyl(3-bromo-2-ethylphenyl)sulfane	HCID 66911124	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Toluene	HCID 1140	—
Product	4-(3-(Benzylthio)-2-ethylphenyl)morpholin-3-one	HCID 66911145	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

Intermediate 4 (1.075 g, 3.5 mmol), morpholin-3-one (389 mg, 3.85 mmol), CuI (67 mg, 0.35 mmol), N,N′-dimethylethylene diamine (75 μl, 0.7 mmol) and K2CO3 (1.064 g, 7.7 mmol) were suspended in toluene (30 ml) under argon and heated to 110° C. for 20 h. After cooling to RT the reaction mixture was quenched by addition of 100 ml sat. aq. NH4Cl, 150 ml concentrated NH3 in water and 100 ml water and extracted three times with ethyl acetate. The organic layers were combined and washed with water and sat. aq. NaCl-solution, dried with MgSO4, filtered and evaporated to dryness. The resulting oil crystallizes upon standing and was triturated with n-heptane-MTBE (19:1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08835653B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-7ec6910c258a42a1b1e945b9df3675f2
Source note	uspto-grants-2014_09