Potassium Carbonate → Methyl 4-(2-oxoimidazolidin-1-yl)benzoate

HRID 1710332Notes

Reaction equation

HRID 1710332 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5](=[O:17])[NH:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[O:17]=[C:5]1[NH:4][CH2:3][CH2:2][N:6]1[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 2345859Methyl 4-(3-(2-chloroethyl)ureido)benzoate

Product 1

HCID 18526090Methyl 4-(2-oxoimidazolidin-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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).

Workup

  1. filtrationThe solid was filtered off
  2. customthe solvent was removed in vacuum
  3. dissolutionThe crude product was dissolved in dichloromethane
  4. custompurified on ISCO system (30% EtOAc in dichloromethane)
  5. customto give a pure product as a white crystalline (5.48 g, 75%)

Sources & evidence

ORD record
ord-c0d4ee3aaa6a4e1da6d7c896e4cf81d1
Source dataset
uspto-grants-2010_09
Patent number
US07790707B2

Reaction notes

Loading…