Reaction #1797514

Reaction equation

Methyl 4-(3-(2-chloroethyl)ureido)benzoate

K2CO3

→

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

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   FiltrationThe solid was filtered off
2. 2
   Otherthe solvent was removed in vacuum
3. 3
   workup.DISSOLUTIONThe crude product was dissolved in dichloromethane
4. 4
   Otherpurified on ISCO system (30% EtOAc in dichloromethane)
5. 5
   Otherto give a pure product as a white crystalline (5.48 g, 75%)

Procedure

Methyl 4-(3-(2-chloroethyl)ureido)benzoate (8.5 g, 33.1 mmol) was then stirred in N,N-dimethylformamide (80 ml) with K2CO3 (2.3 g, 16.7 mmol) at room temperature for 12 hours. The solid was filtered off and the solvent was removed in vacuum. The crude product was dissolved in dichloromethane and purified on ISCO system (30% EtOAc in dichloromethane) to give a pure product as a white crystalline (5.48 g, 75%): 1H NMR (400 MHz, CDCl3) δ 8.00 (d, 2H), 7.62 (d, 2H), 4.90 (br s, 1H), 3.97 (dd, 2H), 3.90 (s, 3H), 3.60 (dd, 2H). MS (ESI) m/z: Calculated: 220.08; Observed: 221.10 (M++1).

Source