4-Chlorobutyrophenone → HCID 13059486, compound

HRID 2198528Notes

Reaction equation

HRID 2198528 reaction equation
[CH3:1][NH:2][C:3](=[S:6])[NH:4][NH2:5].[C:7]1([C:13](=O)[CH2:14][CH2:15][CH2:16]Cl)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)(C)C>[CH3:1][N:2]1[C:3](=[S:6])[NH:4][N:5]2[CH2:16][CH2:15][CH2:14][C:13]12[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 2535334-ChlorobutyrophenoneHCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 13059486HCID 13059486, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4.2 g of 4-methyl-thiosemicarbazide and 8.0 g of 1-phenyl-4-chlorobutan-1-one in 200 ml of isopropanol is refluxed for 48 hours. The solvent is then evaporated and the residue is dissolved in methylene chloride. The resulting solution is washed with saturated aqueous sodium bicarbonate and with saturated aqueous sodium chloride and then dried over sodium sulfate. Evaporation of the solvent leaves a brownish oil which crystallizes partially. This is treated with ether to give a light yellow powder which is purified by flash chromatography, using 10% ethyl acetate/methylene chloride as the eluent to give 5,6,7,7a-tetrahydro-1-methyl-7a-phenyl-1H-pyrrolo[1,2-b][1,2,4]triazole-2(3H)-thione as colorless crystals melting at about 148°-151° C.

Workup

  1. customThe solvent is then evaporated
  2. dissolutionthe residue is dissolved in methylene chloride
  3. washThe resulting 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 partially
  8. additionThis is treated with ether
  9. customto give a light yellow powder which
  10. customis purified by flash chromatography

Sources & evidence

ORD record
ord-c33a57999ee64824a581e2b7345160a9
Source dataset
uspto-grants-1982_11
Patent number
US04358457

Reaction notes

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