HCID 19347471, compound → HCID 19347456, compound

HRID 1638172Notes

Reaction equation

HRID 1638172 reaction equation
Br.[Br:2][CH:3]1[C:14](=[O:15])[C:7]2[N:8]3[N:13]=[CH:12][N:11]=[C:9]3[S:10][C:6]=2[CH2:5][CH2:4]1.N1C=NC(S)=N1>C(O)C>[BrH:2].[N:13]1[N:8]2[C:9]([S:10][C:6]3[CH2:5][CH2:4][CH2:3][C:14](=[O:15])[C:7]=32)=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 19347471HCID 19347471, compoundHCID 178527894HCID 178527894, compound

Product 1

HCID 19347456HCID 19347456, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Bromo-1,3-cyclohexadione (4.4 g) prepared in Example 1, Route 1 (A) and 1H-1,2,4-triazole-3-thiol (2.32 g) were dissolved into absolute ethanol (50 ml), and the reaction mixture was heated to reflux for 5 hours. After completion of the reaction, the reaction mixture was cooled and filtered to give 5,6-dihydro[1,2,4]triazolo[5,1-b]benzothiazole-8(7H)-one hydrobromide (2.84 g, compound (IIc) of Reaction Scheme II). The hydrobromide was dissolved into anhydrous acetic acid (20 ml) and an equivalent amount of bromine was added dropwise thereto at a temperature of 100° C., and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was cooled to give the titled compound (95%) as solids.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 5 hours
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was cooled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-60d3ec185f6043998e5049b06926ba6b
Source dataset
uspto-grants-2000_03
Patent number
US06043373

Reaction notes

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