Phenylhydrazine → HCID 21678987, compound

HRID 850708Notes

Reaction equation

HRID 850708 reaction equation
CCOCC.[N:6]([C:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:13])[C:10]([O-:12])=O)=[C:7]=[S:8].[C:20]1([NH:26]N)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C(C)=CC=CC=1>[C:20]1([N:26]2[C:10](=[O:12])[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([CH3:13])[NH:6][C:7]2=[S:8])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 19364973HCID 19364973, compound

Product 1

HCID 21678987HCID 21678987, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4.7 g (20 mmol) of ether 2-isothiocyanato-2-phenylpropionate are dissolved in 40 ml of xylene. 2.16 g (20 mmol) of phenylhydrazine are added and the mixture is heated for 4 hours at reflux. The mixture is cooled to room temperature and a beige solid precipitates. The precipitate is filtered, washed with 5 ml of diisopropyl ether and then dried under vacuum. 4.6 g (yield=77%) of 3,5-diphenyl-5-methyl-2-thiohydantoin are thus obtained in the form of a beige powder melting at 164° C.

Workup

  1. temperaturethe mixture is heated for 4 hours
  2. temperatureat reflux
  3. customa beige solid precipitates
  4. filtrationThe precipitate is filtered
  5. washwashed with 5 ml of diisopropyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-9fe84e6c311c4da79262d4fc697d2c9d
Source dataset
uspto-grants-2000_01
Patent number
US06018052

Reaction notes

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