Bromine → HCID 19347471, compound

HRID 1638173Notes

Reaction equation

HRID 1638173 reaction equation
[BrH:1].[N:2]1[N:9]2[C:5]([S:6][C:7]3[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[C:8]=32)=[N:4][CH:3]=1.BrBr>C(O)(=O)C>[BrH:1].[Br:1][CH:11]1[C:10](=[O:14])[C:8]2[N:9]3[N:2]=[CH:3][N:4]=[C:5]3[S:6][C:7]=2[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 24408BromineHCID 19347456HCID 19347456, compound

Product 1

HCID 19347471HCID 19347471, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

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 cooled

Sources & evidence

ORD record
ord-3705c7df22a14202a9d8a6c3f8748e33
Source dataset
uspto-grants-2000_03
Patent number
US06043373

Reaction notes

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