Potassium Carbonate → HCID 178526848, compound

HRID 1856802Notes

Reaction equation

HRID 1856802 reaction equation
[OH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:5]([SH:13])=[N:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:21]1[S:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][N:25]=1>C(O)C>[OH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:5]([S:13][C:21]2[S:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][N:25]=2)=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 182112-Bromo-5-nitrothiazoleHCID 178518948HCID 178518948, compound

Product 1

HCID 178526848HCID 178526848, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The title compound was prepared by the general method described by Potts, K. T. (1961) Chem. Rev. 61:87. 4-Phenyl-3-thiosemicarbazide (4.18 g) (Aldrich) was dissolved in 50 mL of pyridine and treated with 2.71 g of ethyl chloroformate at 0° C. The reaction was stirred for 2 hours and then refluxed for 18 hours. Evaporation of the solvent and trituration with water gave 2.5 g of 3-hydroxy-5-mercapto-4-phenyl-1,2,4-triazole. 3-Hydroxy-5-mercapto-4-phenyl-1,2,4-triazole (1.93 g) was stirred in 10 mL of ethanol with 1.1 equivalent of potassium carbonate in 10 mL ethanol for one hour and then reacted with 2.09 g of 2-bromo-5-nitrothiazole as in Example 1. Crystallization from ethanol and water gave 0.6 g of 3-hydroxy-5-[(5-nitrothiazol-2-yl)mercapto]-4-phenyl-1,2,4-triazole, a dark yellow solid, M.P. 188-190° C.

Workup

  1. customCrystallization from ethanol and water

Sources & evidence

ORD record
ord-6dfe6d8a670442f8af634927745a3e0e
Source dataset
uspto-grants-2000_11
Patent number
US06143765

Reaction notes

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