Phenyl isocyanate → 1-Phenylimidazolidin-2-one

HRID 235991Notes

Reaction equation

HRID 235991 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1[CH2:14][CH2:13][NH:12]C1=O.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[C:1]1([N:7]2[CH2:14][CH2:13][NH:12][C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 739492-OxazolidinoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2552731-Phenylimidazolidin-2-oneYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
195 °C

Procedure

A mixture of phenyl isocyanate (50 mmoles), 2-oxazolidinone (50 mmoles) and anhydrous AlCl3 (40 mg, 0.3 mmole) is heated at 195° C. for 6 hours with stirring. The reaction mixture is dissolved in dichloromethane and the resulting solution is washed with water twice. The dichloromethane solution is dried and evaporated and the residue distilled at reduced pressure. The distillate is recrystallized from hot hexane to give a yield of 48 percent of the desired product, m.p. 157° C.-159° C.

Workup

  1. washthe resulting solution is washed with water twice
  2. dry with materialThe dichloromethane solution is dried
  3. customevaporated
  4. distillationthe residue distilled at reduced pressure
  5. customThe distillate is recrystallized from hot hexane

Sources & evidence

ORD record
ord-3ad1493a4bb64af198b2bfca450bccfb
Source dataset
uspto-grants-1987_02
Patent number
US04642351

Reaction notes

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