Acetone → HCID 178482503, compound

HRID 1759005Notes

Reaction equation

HRID 1759005 reaction equation
[CH3:1][NH:2][C:3](=[S:6])[NH:4][NH2:5].CC(C)=O.N1[CH:16]=[CH:15][CH:14]=CC=1.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>O>[CH3:1][NH:2][C:3]1[S:6][C:15]([CH3:14])([CH3:16])[N:5]([C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[N:4]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 178482503HCID 178482503, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 52.5 g. portion of 4-methylthiosemicarbazide was suspended and partially dissolved in 250 ml. of acetone, and 39.5 g. of pyridine was added. The mixture was stirred for 15 minutes at ambient temperature, and then 60.5 g. of pivaloyl chloride was added slowly while the temperature of the reaction mixture was held at 20°-25°. The mixture was stirred at ambient temperature for 3 hours after the addition, and then 200 ml. of water was added. The reaction mixture was filtered, and the filter cake was washed with 100 ml. of nitromethane and vacuum dried at 50° to obtain 91.4 g. of the desired intermediate product, m.p. 162°-164°.

Workup

  1. dissolutionpartially dissolved in 250 ml
  2. customwas held at 20°-25°
  3. stirringThe mixture was stirred at ambient temperature for 3 hours
  4. additionafter the addition
  5. filtrationThe reaction mixture was filtered
  6. washthe filter cake was washed with 100 ml
  7. dry with materialof nitromethane and vacuum dried at 50°
  8. customto obtain 91.4 g

Sources & evidence

ORD record
ord-22c5e778b23a4b27a353e8dc8c6dd367
Source dataset
uspto-grants-1982_07
Patent number
US04338449

Reaction notes

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