Potassium Hydroxide → 5-Phenyl-3H-1,2,4-triazole-3-thione
Reaction equation
[C:1]([NH:9][NH:10][C:11]([NH2:13])=[S:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[K].[O-]CC.[Na+]>C(O)C>[C:2]1([C:1]2[N:9]=[N:10][C:11](=[S:12])[N:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Phenyl-1,2,4-triazole-5-thione (E. Hogarth, J. Chem. Soc. (1949) 1163) was prepared by first reacting benzoyl chloride with thiosemicarbazide in pyridine at 0° C. to give benzoyl thiosemicarbazide. Benzoyl thiosemicarbazide was treated with potassium hydroxide or potassium or sodium ethoxide in ethanol to give 3-phenyl-1,2,4-triazole-5-thione. 3-Phenyl-1,2,4-triazole-5-thione (1.77 g) was then dissolved in 50 mL of methanol and treated with 0.57 g of 95% sodium methoxide, and then with 2-bromo-5-nitrothiazole (2.09 g). The mixture was stirred at room temperature for 2 hours and the precipitated sodium bromide was removed by filtration. The methanol was evaporated and the product crystallized from ethanol and water to give 1.5 g of 3-[(5-nitrothiazol-2-yl)mercapto]-5-phenyl-1,2,4-triazole as colorless crystals, MP 155-157° C.
Sources & evidence
- ORD record
- ord-d76e7dc50f294b238411629f041df8b8
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06080772
Reaction notes
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