Phenylhydrazine → HCID 21678987, compound

HRID 266261Notes

Reaction equation

HRID 266261 reaction equation
[N:1]([C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:10])[C:5]([O:7]CC)=O)=[C:2]=[S:3].[C:17]1([NH:23]N)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C(C)=CC=CC=1>[C:17]1([N:23]2[C:5](=[O:7])[C:4]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)([CH3:10])[NH:1][C:2]2=[S:3])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 18323186HCID 18323186, compound

Product 1

HCID 21678987HCID 21678987, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4.7 g (20 mmol) of ethyl 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-972d33e5f1d74aaa9cc1568fef95da8b
Source dataset
uspto-grants-1997_07
Patent number
US05650519

Reaction notes

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