2-Bromopyridine → 1-(Pyridin-2-yl)imidazolidin-2-one

HRID 458549Notes

Reaction equation

HRID 458549 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].Br[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.CC([O-])=O.[K+]>N1C=CC=CC=1.[Cu].Cl[Cu]>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[N:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6]

Participants

7

Reactant 3

HCID 79732-BromopyridineHCID 84532-ImidazolidinoneHCID 517044Potassium Acetate

Product 1

HCID 2942411-(Pyridin-2-yl)imidazolidin-2-one

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 62652Cuprous chlorideCatalystHCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-imidazolidinone (1.00 g, 11.6 mmol), 2-bromopyridine (3.40 mL, 34.8 mmol), copper powder (2.58 g, 40.7 mmol), CuCl (230 mg, 2.32 mmol), and KOAc (3.99 g, 40.7 mmol) in pyridine (10 mL) was heated at 60° C. for 18 h. The cooled mixture was partitioned between CHCl3 (100 mL) and 10% aqueous citric acid (50 mL). The aqueous layer was adjusted to pH 11 with 10 N aqueous NaOH, extracted with CHCl3 (3×100 mL), and these organic layers were combined and dried over Na2SO4, filtered, and concentrated under reduced pressure, to give the title compound in sufficient purity for use in the next step. MS: m/z=164 (M+1).

Workup

  1. customThe cooled mixture was partitioned between CHCl3 (100 mL) and 10% aqueous citric acid (50 mL)
  2. extractionextracted with CHCl3 (3×100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f379389fd1b14fe79a1dfcea37441ee9
Source dataset
uspto-grants-2007_03
Patent number
US07192954B2

Reaction notes

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