Hydrochloric Acid → 1-Phenylimidazolidine-2,4-dione

HRID 1380068

Reaction equation

HRID 1380068 reaction equation
[C:1]1([NH:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-:12][C:13]#[N:14].[K+].Cl>O.C(O)(=O)C>[C:1]1([N:7]2[CH2:8][C:9](=[O:11])[NH:14][C:13]2=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 66025N-PhenylglycineHCID 11378442Potassium cyanate

Product 1

HCID 5705761-Phenylimidazolidine-2,4-dioneYield 24.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

A solution of N-phenylglycine (Fluka) (30.2 g, 0.2 moles) in 900 ml of water and 1 ml of acetic acid was heated to 60° C. After thirty minutes potassium cyanate (16.2 g, 0.2 moles) in 100 ml of water was added. Heating was continued for 90', then 25 ml of 37% hydrochloric acid were added and the reaction mixture was heated for 15 h at 90° C. After cooling the precipitate was filtered and crystallized from 95% ethanol. 8.65 g of 1-phenylhydantoin were obtained, m.p. 197°-198°.

Workup

  1. temperatureHeating
  2. additionwere added
  3. temperatureAfter cooling the precipitate
  4. filtrationwas filtered
  5. customcrystallized from 95% ethanol

Sources & evidence

ORD record
ord-0a835e460ff94148a71c2fd8497e562b
Source dataset
uspto-grants-1986_04
Patent number
US04579861

Linked notes

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