Water → HCID 178424798, compound

HRID 1388995Notes

Reaction equation

HRID 1388995 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][CH2:10][C:11]([NH:13][NH:14][C:15]([NH:17][CH3:18])=[S:16])=O.[OH-].[Na+].O>C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][CH2:10][C:11]1[N:17]([CH3:18])[C:15]([SH:16])=[N:14][N:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13825449HCID 13825449, compound

Product 1

HCID 178424798HCID 178424798, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred hot solution of 52.8 g (0.198 mol) 1[alpha-(2,6-dimethylphenylamino)acetyl]-4-methylthiosemicarbazide in 560 ml ethanol was added quickly 8 g (0.198 mol) sodium hydroxide. The reaction mixture was heated under reflux for 2 hours and allowed to stand overnight. The ethanol was then evaporated under reduced pressure to give a solid residue. Water (500 ml) was added to the solid residue and the resulting aqueous mixture was filtered to remove a small amount of a solid. The filtrate was neutralized with concentrated hydrochloric acid, the colorless solid was filtered, washed with water and partially dried in vacuuo over potassium hydroxide pellets at 50° C. The nearly dried product was dissolved in dichloromethane and the aqueous layer separated. The organic layer was dried over magnesium sulfate, filtered and evaporated under reduced pressure to give 43.5 g of the product as a colorless solid, m.p. 172°-173° C. The product is tabulated in Table I as Compound No. 3.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customThe ethanol was then evaporated under reduced pressure
  4. customto give a solid residue
  5. filtrationthe resulting aqueous mixture was filtered
  6. customto remove a small amount of a solid
  7. filtrationthe colorless solid was filtered
  8. washwashed with water
  9. dry with materialpartially dried in vacuuo over potassium hydroxide pellets at 50° C
  10. dissolutionThe nearly dried product was dissolved in dichloromethane
  11. customthe aqueous layer separated
  12. dry with materialThe organic layer was dried over magnesium sulfate
  13. filtrationfiltered
  14. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9d18e70bd8224a4daa6673e35ad17540
Source dataset
uspto-grants-1981_01
Patent number
US04243408

Reaction notes

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