1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate → 2-(Cyclopropylamino)-4,5,6-trichloro-1H-benzimidazole

Participants

Role	Name	HCID	Charge
Reactant	1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate	HCID 17220	—
Reactant	Cyclopropyl isothiocyanate	HCID 92463	—
Reactant	3,4,5-Trichlorobenzene-1,2-diamine	HCID 100529	—
Solvent	Pyridine	HCID 1049	—
Product	2-(Cyclopropylamino)-4,5,6-trichloro-1H-benzimidazole	HCID 22995411	83.3%

Reaction Steps

3,4,5-Trichloro-1,2-phenylenediamine (3.02 g, 14.28 mmol), cyclopropyl isothiocyanate (1.53 g, 15.42 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (8.24 g, 19.45 mmol) and pyridine (55 mL) were used according to general procedure I. The product was recrystallized from 1,4-dioxane to afford 3.29 g (83%) of a white solid. MS (CI): m/z 274. Anal. Calcd for C10H8Cl3N3-(0.6 C4H8O2): C, 45.21; H, 3.92; N, 12.76. Found: C, 45.37; H, 3.91; N, 12.76.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06204249B1
Source dataset	uspto-grants-2001_03
ORD ID	ord-f2335d1862ea49dfaee8d52e84d4de56
Source note	uspto-grants-2001_03