Methanol → 3-Bromopropiophenone thiosemicarbazone

HRID 1921591Notes

Reaction equation

HRID 1921591 reaction equation
[Br:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.CO.[NH2:14][NH:15][C:16]([NH2:18])=[S:17]>CC(O)=O>[Br:1][CH2:2][CH2:3][C:4](=[N:14][NH:15][C:16]([NH2:18])=[S:17])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1224323-Bromo-1-phenylpropan-1-oneHCID 2723789Thiosemicarbazide

Product 1

HCID 866288273-Bromopropiophenone thiosemicarbazoneYield 42.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(Du, X.; Guo, C.; Hansell, E.; Doyle, P. S.; Caffrey, C. R.; Holler, T. P.; McKerrow, J. H.; Cohen, F. E. J. Med. Chem. 2002, 45, 2695-2707) Into a round bottom flask containing 3-bromopropiophenone (0.508 g, 2.34 mmol), 20 mL of anhydrous methanol were added and the solution was refluxed for 15 minutes. To the warm ketone solution, thiosemicarbazide (0.184 g, 2.04 mmol) and 1% solution of HOAc (0.2 mL) were added. The reaction mixture was refluxed under nitrogen atmosphere for 17 h, at which point, the solvent was evaporated and, the crude reaction mixture was purified by flash chromatography (30% EtOAc/70% hex) to obtain 0.2498 g (0.873 mmol) of the product in a 37% yield.

Workup

  1. additionwere added
  2. temperaturethe solution was refluxed for 15 minutes
  3. temperatureThe reaction mixture was refluxed under nitrogen atmosphere for 17 h, at which point
  4. customthe solvent was evaporated
  5. customthe crude reaction mixture
  6. customwas purified by flash chromatography (30% EtOAc/70% hex)

Sources & evidence

ORD record
ord-fc12a2f8699b427d95bd82c55176c585
Source dataset
uspto-grants-2012_05
Patent number
US08173696B2

Reaction notes

Loading…