Hydrochloric Acid → 4-phenyl-2,3-dihydro-1H-imidazol-2-one

HRID 1584654Notes

Reaction equation

HRID 1584654 reaction equation
[NH2:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[O-:11][C:12]#[N:13].[K+].Cl>O>[C:5]1([C:3]2[NH:13][C:12](=[O:11])[NH:1][CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11952PhenacylamineHCID 11378442Potassium cyanate2×

Product 1

HCID 110626774-phenyl-2,3-dihydro-1H-imidazol-2-oneYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

2-Aminoacetophenone (5.6 g, 32.65 mmol) was dissolved in 200 ml of water in a three necked flask equipped with a thermometer and was heated up to 70° C. Potassium cyanate (2.9 g, 35.92 mmol) was added in several portions at 70° C. while the pH of the reaction solution was maintained in the range of 1 to 3 by the continuous addition of conc. HCl. After the addition of potassium cyanate was completed, the reaction mixture was stirred at 70° C. for 4 hours and left at room temperature overnight. The brownish precipitate thus formed was collected by filtration and dried to obtain 3.7 g of the title compound.

Workup

  1. customequipped with a thermometer
  2. waitleft at room temperature overnight
  3. customThe brownish precipitate thus formed
  4. filtrationwas collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-eeb820c51e604037aaec8b63978e9f95
Source dataset
uspto-grants-1999_08
Patent number
US05932742

Reaction notes

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