Acetonitrile → Tert-butyl 2-oxoimidazolidine-1-carboxylate

HRID 322509Notes

Reaction equation

HRID 322509 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[C:9]1=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC#N>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:20])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 12028338Di-tert-butyl 2-oxoimidazolidine-1,3-dicarboxylate

Product 1

HCID 22008758Tert-butyl 2-oxoimidazolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 6-2 (28.0 g, 98 mmol), Mg(ClO4)2 (4.3 g, 20 mmol), and CH3CN (400 mL) was heated at 50° C. for 3 hr. The cooled solution was diluted with CHCl3 and then washed with 1N HCl, sat. naHCO3, and brine, dried (Mg SO4), and concentrated. Flash chromatography (silica, 50% EtOAc/hexanes→EtOAc) gave 6-3 as a yellow solid.

Workup

  1. washwashed with 1N HCl
  2. dry with materialsat. naHCO3, and brine, dried (Mg SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e4f41543a3594a02b8589540421b6984
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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