Acetic Acid → HCID 18323161, compound

HRID 266262Notes

Reaction equation

HRID 266262 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].O.C(O)(=O)C>O1CCCC1>[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

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 786452-HydrazinopyridineHCID 18323185HCID 18323185, compound

Product 1

HCID 18323161HCID 18323161, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

2 g (9 mmol) of methyl 2-isothiocyanato-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 met 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. additionA solution containing 1 g of potassium tert-butoxide and 10 ml of tetrahydrofuran
  5. additionis then added
  6. waitThe mixture is left
  7. customto return to room temperature
  8. waitis left
  9. customto react for 2 hours
  10. extractionThe product is extracted with 150 ml of ethyl acetate
  11. washThe solution is washed with water
  12. dry with materialdried over magnesium sulfate
  13. additiontreated with active charcoal
  14. concentrationThe solution is concentrated
  15. customthe product is crystallized from 20 ml of diethyl ether
  16. filtrationThe above-mentioned product is filtered
  17. customis dried under vacuum

Sources & evidence

ORD record
ord-ad8a8ec5b5914a3fafa3b85f28eadeb6
Source dataset
uspto-grants-1997_07
Patent number
US05650519

Reaction notes

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