Hydrochloric Acid → 3-(4-Chloro-3-(trifluoromethyl)phenyl)-5,5-dimethyl-2,4-imidazolidinedione

HRID 647126Notes

Reaction equation

HRID 647126 reaction equation
CO[C:3](=[O:22])[C:4]([CH3:21])([CH3:20])[NH:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=1.Cl>CC(C)=O>[F:18][C:15]([F:16])([F:17])[C:10]1[CH:9]=[C:8]([N:7]2[C:3](=[O:22])[C:4]([CH3:20])([CH3:21])[NH:5][C:6]2=[O:19])[CH:13]=[CH:12][C:11]=1[Cl:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 3054076Propanoic acid, 2-((((4-chloro-3-(trifluoromethyl)phenyl)amino)carbonyl)amino)-2-methyl-, methyl ester

Product 1

HCID 30540783-(4-Chloro-3-(trifluoromethyl)phenyl)-5,5-dimethyl-2,4-imidazolidinedione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 8.00 g. of N-[(3-trifluoromethyl-4-chloro-phenyl)-carbamoyl]-2-methylalanine methyl ester in 20 ml. of 6-N aqueous hydrochloric acid and 20 ml. of acetone are warmed on a steam bath for 2 hours and the mixture is then concentrated. The product which has precipitated is first recrystallized from methylene chloride and then from methylene chloride/petroleum ether. After drying under greatly reduced pressure at 50° for 20 hours, 3-(3-trifluoromethyl-4-chloro-phenyl)-5,5-dimethylhydantoin of melting point 152°-153° is obtained.

Workup

  1. concentrationthe mixture is then concentrated
  2. customThe product which has precipitated
  3. customis first recrystallized from methylene chloride
  4. customAfter drying under greatly reduced pressure at 50° for 20 hours

Sources & evidence

ORD record
ord-cb74ec252d7c4603a75ce0cc0f3f36b6
Source dataset
uspto-grants-1983_10
Patent number
US04407814

Reaction notes

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