Water → HCID 18323161, compound

HRID 613766Notes

Reaction equation

HRID 613766 reaction equation
[N:1]([C:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:9])[C:5]([O:7]C)=O)=[C:2]=[S:3].[NH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[NH2:17].CC(C)([O-])C.[K+].O>O1CCCC1.C(O)(=O)C>[CH3:9][C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:1][C:2](=[S:3])[N:17]([NH:16][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[C:5]1=[O:7]

Participants

7

Reactant 4

HCID 962WaterHCID 786452-HydrazinopyridineHCID 18323185HCID 18323185, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18323161HCID 18323161, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

2 g (9 mmol) of methyl 2isothiocyanato-2-phenylpropionate are dissolved in 30 ml of tetrahydrofuran. A solution containing 0.99 g of 2 -hydrazinopyridine and 10 ml of tetrahydrofuran is added: the temperature of the mixture rises from 20 to 30° C. and a solid precipitates. The mixture is allowed to react for 0.5 hour at 30° C. and then is cooled to 5° c. A solution containing 1 g of potassium tert-butoxide and 10 ml of tetrahydrofuran is then added: the mixture becomes violet in color. The mixture is left to return to room temperature and is left to react for 2 hours. The mixture is poured into 150 ml of water. The mixture is neutralized with acetic acid. The product is extracted with 150 ml of ethyl acetate. The solution is washed with water, dried over magnesium sulfate and then treated with active charcoal. The solution is concentrated and the product is crystallized from 20 ml of diethyl ether. The above-mentioned product is filtered and is dried under vacuum. 1.6 g (yield: 60%) of 5-methyl-5-phenyl-3-(2-pyridylamino)-2-thiohydantoin is obtained as a pale-yellow solid melting at 80° C.

Workup

  1. additionis added
  2. customrises from 20 to 30° C.
  3. customa solid precipitates
  4. customto react for 0.5 hour at 30° C.
  5. temperatureis cooled to 5° c
  6. additionis then added
  7. waitThe mixture is left
  8. customto return to room temperature
  9. waitis left
  10. customto react for 2 hours
  11. extractionThe product is extracted with 150 ml of ethyl acetate
  12. washThe solution is washed with water
  13. dry with materialdried over magnesium sulfate
  14. additiontreated with active charcoal
  15. concentrationThe solution is concentrated
  16. customthe product is crystallized from 20 ml of diethyl ether
  17. filtrationThe above-mentioned product is filtered
  18. customis dried under vacuum

Sources & evidence

ORD record
ord-27b93c3ac68748fa9299ac3a210a7894
Source dataset
uspto-grants-1999_12
Patent number
US06008370

Reaction notes

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