Benzoyl chloride → 1-Benzoylimidazolidin-2-one

HRID 1283018Notes

Reaction equation

HRID 1283018 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].O1CCCC1.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[C:12]([N:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8028Tetrahydrofuran2×HCID 84532-ImidazolidinoneHCID 516892Sodium Bicarbonate

Product 1

HCID 5696651-Benzoylimidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
10 °C

Procedure

8.6 parts by weight of imidazolid-2-one in 100 parts by volume of dry tetrahydrofurane were treated with 15.5 parts by weight of benzoyl chloride in 30 parts by volume of tetrahydrofurane over the course of 15 minutes, at 5°-10°C, and the mixture was subsequently stirred for 3 hours at 10°C. The solvent was stripped off, the residue was shaken with a mixture of chloroform and aqueous NaHCO3 solution for 15 minutes, the chloroform was separated off, the water was again extracted with chloroform and the combined organic phases were washed with water, dried over MgSO4 and evaporated. The residue was recrystallized from ethyl acetate/ether.

Workup

  1. customthe chloroform was separated off
  2. extractionthe water was again extracted with chloroform
  3. washthe combined organic phases were washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was recrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-49382d9603cc462e8a52570178f2ea8d
Source dataset
uspto-grants-1976_08
Patent number
US03974141

Reaction notes

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