Reacción #1797514

ord-c0d4ee3aaa6a4e1da6d7c896e4cf81d1

Ecuación de reacción

COC(=O)c1ccc(NC(=O)NCCCl)cc1
Methyl 4-(3-(2-chloroethyl)ureido)benzoate
O=C([O-])[O-].[K+].[K+]
K2CO3
COC(=O)c1ccc(N2CCNC2=O)cc1
Methyl 4-(2-oxoimidazolidin-1-yl)benzoate

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07790707B2uspto-grants-2010_09