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

HRID 866487

Reaction equation

HRID 866487 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.CS(O)(=O)=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

5

Reactant 3

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 595293N-[[(3,5-dichlorophenyl)amino]carbonyl]glycine

Product 1

HCID 1686913-(3,5-Dichlorophenyl)-2,4-imidazolidinedioneYield 95.3%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
15 °C

Procedure

To a suspension of 3-(3,5-dichlorophenyl)-ureidoacetic acid (526 g.) in chlorobenzene (2,250 cc.) is added methanesulphonic acid (d = 1.48) (10 cc., representing 0.077 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 (467 g.) melting at 199° C is obtained. Yield: 94%.

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-3c3722fd6f2d44169a5439e24aec2148
Source dataset
uspto-grants-1978_07
Patent number
US04099008

Linked notes

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