Reaction #1797515

Reaction equation

Methyl 4-(2-oxoimidazolidin-1-yl)benzoate

iodo-1-tert-butyl-4-iodobenzene

K3PO4

N,N′-dimethyl ethylenediamine

→

Methyl 4-(3-(4-tert-butylphenyl)-2-oxoimidazolidin-1-yl)benzoate

Solvents

1,4-dioxane

Conditions

Workup

1. 1
   Otherthe solvent was removed in vacuum
2. 2
   Otherpurified on ISCO system (5% methanol in dichloromethane)
3. 3
   Otherto give a pure product as a white crystalline (275 mg, 78%)

Procedure

Methyl 4-(2-oxoimidazolidin-1-yl)benzoate (220 mg, 1.0 mmole) was mixed with iodo-1-tert-butyl-4-iodobenzene (260 mg, 1.0 mmol), CuI (38 mg, 0.2 mmol), K3PO4 (426 mg, 2 mmol), N,N′-dimethyl ethylenediamine (17 mg, 0.2 mmol) and 1,4-dioxane (5 ml). The mixture was heated at 110° C. with stirring for 12 hours, and the solvent was removed in vacuum. The residue was suspended in dichloromethane and purified on ISCO system (5% methanol in dichloromethane) to give a pure product as a white crystalline (275 mg, 78%): 1H NMR (400 MHz, CDCl3) δ 8.05 (dd, 2H), 7.70 (dd, 2H), 7.36 (dd, 2H), 7.20 (dd, 2H), 4.02 (s, 4H), 3.90 (s, 3H), 1.30 (s, 9H). MS (ESI) m/z: Calculated: 352.18; Observed: 353.10 (M++1).

Source