Acetone → 3,4-Dimethyl-2(3H)thiazolone-(1-methylethylidene)hydrazone

HRID 33082

Reaction equation

HRID 33082 reaction equation
[CH3:1][NH:2][C:3](=[S:6])[NH:4][NH2:5].Cl[CH2:8][C:9](=O)[CH3:10].[CH3:12][C:13]([CH3:15])=O>>[CH3:8][C:9](=[N:5][N:4]=[C:3]1[N:2]([CH3:1])[C:13]([CH3:15])=[CH:12][S:6]1)[CH3:10]

Participants

4

Reactant 3

HCID 180AcetoneHCID 6571ChloroacetoneHCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 734148093,4-Dimethyl-2(3H)thiazolone-(1-methylethylidene)hydrazone

Procedure

21 g (200 mmol) of 4-methyl-3-thiosemicarbazide in 1000 mL of acetone was heated at reflux for 2 hours. To this solution was then added dropwise 20.4 g (220 mmol) of chloroacetone. The reaction mixture was allowed to reflux for 7 hours and was then concentrated. The resulting crude product was recrystallized from acetone. This gave 23 g of an orange-colored powder (63% of the theoretical).

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureto reflux for 7 hours
  3. concentrationwas then concentrated
  4. customThe resulting crude product was recrystallized from acetone

Sources & evidence

ORD record
ord-9152d2e5710b4945a499398c63afce63
Source dataset
uspto-grants-2008_09
Patent number
US07429274B2

Linked notes

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