p-Toluidine → 3,5-Dimethyl-N-(4-methylphenyl)benzenamine

Participants

Role	Name	HCID	Charge
Reactant	p-Toluidine	HCID 7813	—
Reactant	Dodecane	HCID 8182	—
Reactant	Ammonium Hydroxide	HCID 14923	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	Diethylsalicylamide	HCID 88006	—
Reactant	Benzene, 1-bromo-3,5-dimethyl-	HCID 136357	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	3,5-Dimethyl-N-(4-methylphenyl)benzenamine	HCID 9813156	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

CuI (10 mg, 0.05 mmol), N,N-diethylsalicylamide (10 mg, 0.05 mmol), 4-toluidine (161, 1.5 mmol) and K3PO4 (425 mg, 2.0 mmol) were put into a screw-capped test tube with a Teflon-lined septum. The tube was then evacuated and backfilled with argon (3 cycles). 5-Bromo-m-xylene (136 μL, 1.0 mmol) was added by a syringe. The reaction mixture was stirred at 100° C. for 20 h. The reaction mixture was allowed to reach room temperature. Ethyl acetate (˜2 mL), water (˜10 mL), ammonium hydroxide (˜0.5 mL) and dodecane (227 μL) were added. The organic phase was analyzed by GC and 22% conversion of 5-bromo-m-xylene and 9% GC yield of the desired product was obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07115784B2
Source dataset	uspto-grants-2006_10
ORD ID	ord-d1e0b7aacb3b47a48ecfb9031e0a32c7
Source note	uspto-grants-2006_10