1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → Hydantoin, 3-(4-chloro-alpha,alpha,alpha-trifluoro-m-tolyl)-5,5-diethyl-

HRID 224948Notes

Reaction equation

HRID 224948 reaction equation
ClC1C=CC(N=C=O)=CC=1C(F)(F)F.COC(=O)C(N)(CC)CC.C[O:26][C:27](=O)[C:28]([NH:33][C:34](=[O:47])[NH:35][C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([C:43]([F:46])([F:45])[F:44])[CH:37]=1)([CH2:31][CH3:32])[CH2:29][CH3:30]>CC(C)=O.Cl>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([N:35]2[C:27](=[O:26])[C:28]([CH2:29][CH3:30])([CH2:31][CH3:32])[NH:33][C:34]2=[O:47])=[CH:37][C:38]=1[C:43]([F:44])([F:45])[F:46]

Participants

6

Reactant 3

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 13412527Methyl 2-amino-2-ethylbutanoateHCID 134125292-(N-[(4-chloro-3-trifluoromethylphenyl)-carbamoyl]-amino)-2-ethylbutyric acid methyl ester

Product 1

HCID 3054229Hydantoin, 3-(4-chloro-alpha,alpha,alpha-trifluoro-m-tolyl)-5,5-diethyl-

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

An admixture of 6.65 g (30 mmol) of 4-chloro-3-trifluoromethylphenyl-isocyanate and 4.4 g (30 mmol) of 2-amino-2-ethyl-butyric acid methyl ester were heated to 100° C. and maintained at that temperature for 5 minutes. The resulting crude product, 2-(N-[(4-chloro-3-trifluoromethylphenyl)-carbamoyl]-amino)-2-ethylbutyric acid methyl ester, was heated for 8 hours on a steam bath in a mixture of 200 ml of acetone and 200 ml of 6 N HCl. The mixture was cooled and then extracted with methylene chloride. The extract was dried over sodium sulphate and the methylene chloride was evaporated. The residue was crystallized from petroleum ether and then from methylene chloride/hexane to yield 3-(4-chloro-3-trifluoromethylphenyl)-5,5-diethyl-hydantoin, m.p. 86°-87° C.

Workup

  1. temperaturemaintained at that temperature for 5 minutes
  2. temperatureThe mixture was cooled
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract was dried over sodium sulphate
  5. customthe methylene chloride was evaporated
  6. customThe residue was crystallized from petroleum ether

Sources & evidence

ORD record
ord-76890b7b13c940bd89ca847f14276008
Source dataset
uspto-grants-1980_11
Patent number
US04234736

Reaction notes

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