4-Chlorobutyrophenone → HCID 13059487, compound

HRID 2198529Notes

Reaction equation

HRID 2198529 reaction equation
[CH3:1][N:2]([C:4]([NH:6][CH3:7])=[S:5])[NH2:3].[C:8]1([C:14](=O)[CH2:15][CH2:16][CH2:17]Cl)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(O)(C)C>[CH3:7][N:6]1[C:4](=[S:5])[N:2]([CH3:1])[N:3]2[CH2:17][CH2:16][CH2:15][C:14]12[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 2535334-ChlorobutyrophenoneHCID 30341872,4-Dimethylthiosemicarbazide

Product 1

HCID 13059487HCID 13059487, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4.0 g of 2,4-dimethyl-thiosemicarbazide and 6.7 g of 1-phenyl-4-chlorobutan-1-one in 165 ml of isopropanol is refluxed for 48 hours. The mixture is then allowed to cool to room temperature and stirred for an additional 48 hours. The solvent is evaporated, the residue is dissolved in methylene chloride, and the methylene chloride solution is washed with saturated aqueous sodium bicarbonate and with saturated aqueous sodium chloride and dried over sodium sulfate. Evaporation of the solvent leaves a brownish oil which crystallizes and is treated with hexane. The resulting greyish powder is purified by flash chromatography using 4% ethyl acetate/methylene chloride as eluent, followed by crystallization from hexane to give 5,6,7,7a-tetrahydro-1,3-dimethyl-7a-phenyl-1H-pyrrolo[1,2-b][1,2,4]triazole-2(3H)-thione as tiny colorless needles melting at about 83°-85° C.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue is dissolved in methylene chloride
  3. washthe methylene chloride solution is washed with saturated aqueous sodium bicarbonate and with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent
  6. customleaves a brownish oil which
  7. customcrystallizes
  8. additionis treated with hexane
  9. customThe resulting greyish powder is purified by flash chromatography
  10. customfollowed by crystallization from hexane

Sources & evidence

ORD record
ord-dfa80c8843bc47b1b468c5b154cecdb9
Source dataset
uspto-grants-1982_11
Patent number
US04358457

Reaction notes

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