Potassium Carbonate → [3-(2-Oxo-imidazolidin-1-yl)-phenyl]-carbamic acid tert-butyl ester

HRID 386469Notes

Reaction equation

HRID 386469 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]([NH:17][CH2:18][CH2:19]Cl)=[O:16])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[H-].[Na+]>O1CCCC1>[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:19][CH2:18][NH:17][C:15]2=[O:16])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 67229696{3-[3-(2-Chloro-ethyl)-ureido]-phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 65143068[3-(2-Oxo-imidazolidin-1-yl)-phenyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of {3-[3-(2-chloro-ethyl)-ureido]-phenyl}-carbamic acid tert-butyl ester (1 g, 3.2 mmol) and potassium carbonate (1.32 g, 9.6 mmol) in dry tetrahydrofuran (20 ml) were stirred at room temperature overnight. No reaction was observed. Sodium hydride (260 mg, 6.5 mmol, 60% dispersion in oil) was then added and reaction stirred at room temperature overnight. Reaction was quenched with water (50 ml) then extracted with dichloromethane (3×50 ml). The combined organics were dried (magnesium sulphate) and concentrated in vacuo. HPLC retention time 7.0 min. Mass spectrum (ES+) m/z 295 (M+NH4)

Workup

  1. customreaction
  2. customReaction
  3. customwas quenched with water (50 ml)
  4. extractionthen extracted with dichloromethane (3×50 ml)
  5. dry with materialThe combined organics were dried (magnesium sulphate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc5b8f1857d9436f9a72531aae194e9a
Source dataset
uspto-grants-2013_02
Patent number
US08372840B2

Reaction notes

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