Methanol → 3-Nitropropiophenone thiosemicarbazone

HRID 1921592Notes

Reaction equation

HRID 1921592 reaction equation
[N+:1]([CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=O)([O-:3])=[O:2].CO.[NH2:16][NH:17][C:18]([NH2:20])=[S:19]>CC(O)=O>[N+:1]([CH2:4][CH2:5][C:6](=[N:16][NH:17][C:18]([NH2:20])=[S:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 5694913-Nitro-1-phenylpropan-1-oneHCID 2723789Thiosemicarbazide

Product 1

HCID 866288283-Nitropropiophenone thiosemicarbazoneYield 60.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Into a round bottom flask containing 3-nitropropiophenone (1.02 g, 5.53 mmol), 30 mL of anhydrous methanol were added and the solution was refluxed for about 15 minutes. To the warm ketone solution, thiosemicarbazide (0.485 g, 5.33 mmol) and 1% solution of HOAc (0.4 mL) were added. The reaction mixture was refluxed under nitrogen atmosphere for 30 h, at which point, the solvent was evaporated and, the crude reaction mixture was purified by flash chromatography (50% EtOAc/50% hex) to obtain 0.8119 g (3.22 mmol) of the product in a 58% yield.

Workup

  1. additionwere added
  2. temperaturethe solution was refluxed for about 15 minutes
  3. temperatureThe reaction mixture was refluxed under nitrogen atmosphere for 30 h, at which point
  4. customthe solvent was evaporated
  5. customthe crude reaction mixture
  6. customwas purified by flash chromatography (50% EtOAc/50% hex)

Sources & evidence

ORD record
ord-157b7d9d87534e4b93beba76647476b8
Source dataset
uspto-grants-2012_05
Patent number
US08173696B2

Reaction notes

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