Water → 3-(3,5-Dichlorophenyl)-2,4-imidazolidinedione

HRID 866486

Reaction equation

HRID 866486 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:16])[NH:11][CH2:12][C:13](O)=[O:14])[CH:5]=[C:6]([Cl:8])[CH:7]=1.S(=O)(=O)(O)O.N(CC(O)=O)C(N)=O.O>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[CH2:12][NH:11][C:10]2=[O:16])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 10020Hydantoic acidHCID 595293N-[[(3,5-dichlorophenyl)amino]carbonyl]glycine

Product 1

HCID 1686913-(3,5-Dichlorophenyl)-2,4-imidazolidinedioneYield 95.6%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
15 °C

Procedure

To a suspension of 3-(3,5-dichlorophenyl)-ureidoacetic acid (813 g.) in chlorobenzene (3,500 cc.) is added concentrated sulphuric acid (d = 1.83) (16 cc.), representing 0.095 mol per mol of ureidoacetic acid. The water formed in the reaction is removed by azeotropic distillation. After 45 minutes' distillation, a limpid solution is obtained. After cooling to about 15° C, the precipitate formed is filtered off and washed on the filter with ethanol (500 cc.) at 10° C. After drying, 3-(3,5-dichlorophenyl)-hydantoin (724 g.) melting at 199° C is obtained. Yield: 95.4%.

Workup

  1. customis removed by azeotropic distillation
  2. distillationAfter 45 minutes' distillation
  3. customa limpid solution is obtained
  4. customthe precipitate formed
  5. filtrationis filtered off
  6. washwashed on the
  7. filtrationfilter with ethanol (500 cc.) at 10° C
  8. customAfter drying

Sources & evidence

ORD record
ord-be996351cfeb41cdad920d3b577d1ac0
Source dataset
uspto-grants-1978_07
Patent number
US04099008

Linked notes

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