Aniline → 1-Phenylimidazolidin-2-one

HRID 1194623Notes

Reaction equation

HRID 1194623 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:8]1[CH2:12][C:11](=O)[N:10]=[C-:9]1>[O-2].[O-2].[Ti+4]>[C:2]1([N:1]2[CH2:12][CH2:11][NH:10][C:9]2=[O:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 532495662H-1,3-oxazol-2-id-4-one

Product 1

HCID 2552731-Phenylimidazolidin-2-oneYield 47%

Reagents, catalysts & solvents 1

HCID 162651Titanium oxide (Ti3O)Catalyst

Conditions

Temperature
0 °C

Procedure

Aniline (15.40 g; 0.165 mole) and 2-oxazolidone (9.60 g; 0.110 mole) were refluxed for 6.5 hours with 1.00 g (0.0125 mole) of titanium dioxide (Harshaw Ti 0720 which had been calcined at 300° C. for 4 hours). The reaction mass was cooled to 0° C. and the crystals which had formed were filtered off. The crystals were recrystallized from ethanol to give N-phenylimidazolidone in 47% yield. The conversion based on 2-oxazolidone was 99%.

Workup

  1. customthe crystals which had formed
  2. filtrationwere filtered off
  3. customThe crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-b2466abfa70042149f223bb986a40272
Source dataset
uspto-grants-1989_03
Patent number
USRE032896

Reaction notes

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