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

HRID 866488

Reaction equation

HRID 866488 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.C1(S(O)(=O)=O)C=CC=CC=1.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

5

Reactant 3

HCID 962WaterHCID 7371Benzenesulfonic AcidHCID 595293N-[[(3,5-dichlorophenyl)amino]carbonyl]glycine

Product 1

HCID 1686913-(3,5-Dichlorophenyl)-2,4-imidazolidinedioneYield 90.6%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
15 °C

Procedure

To a suspension of 3-(3,5-dichlorophenyl)-ureidoacetic acid (26.3 g.) in chlorobenzene (180 cc.) is added benzenesulphonic acid (1.2 g. representing 0.068 mol per mol of ureidoacetic acid). The water formed in the reaction is removed by azeotropic distillation. After 30 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 (25 cc.) at 10° C. After drying, 3-(3,5-dichlorophenyl)-hydantoin (22.2 g.) melting at 199° C is obtained. Yield: 90.5%.

Workup

  1. customis removed by azeotropic distillation
  2. distillationAfter 30 minutes' distillation
  3. customa limpid solution is obtained
  4. customthe precipitate formed
  5. filtrationis filtered off
  6. washwashed on the
  7. filtrationfilter with ethanol (25 cc.) at 10° C
  8. customAfter drying

Sources & evidence

ORD record
ord-c2f494f9b56c4c209ba7eec1f8842a1e
Source dataset
uspto-grants-1978_07
Patent number
US04099008

Linked notes

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