Triethylamine → 4-[3-(4-Methylphenyl)-5-imino-4,4-dimethyl-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	4-Isothiocyanato-2-(trifluoromethyl)benzonitrile	HCID 11615540	—
Reactant	2-Methyl-2-[(4-methylphenyl)amino]propanenitrile	HCID 21239243	—
Reactant	Propan-2-one--dichloromethane (1/1)	HCID 21584124	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	4-[3-(4-Methylphenyl)-5-imino-4,4-dimethyl-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile	HCID 15951818	17%

Reaction Conditions

Temperature	0 °C

Reaction Steps

Triethylamine (0.101 g, 1 mmol) was added to a solution of 1a (0.456 g, 2 mmol) and 5a (0.348 g, 2 mmol) in dry THF (3 ml). The reaction mixture was stirred at 0° C. for 2 days and then concentrated to yield a dark residue which was subjected to flash chromatography (dichloromethane/acetone, 95:5) to afford 4-[3-(4-methylphenyl)-5-imino-4,4-dimethyl-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile, 5b (0.136 g, 0.34 mmol, 17%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08658681B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-672fc72e07f74006bd18aeb2002a59bf
Source note	uspto-grants-2014_02