Bromine → HCID 21717670, compound

HRID 1386117Notes

Reaction equation

HRID 1386117 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[S:15][CH:16]=[CH:17][C:18]=2[CH3:19])[N:11]([CH3:20])[N:10]=1.[Br:21]Br>C(O)(=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[S:15][C:16]([Br:21])=[CH:17][C:18]=2[CH3:19])[N:11]([CH3:20])[N:10]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 15544234HCID 15544234, compound

Product 1

HCID 21717670HCID 21717670, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3-(2-fluoro-6-chlorophenyl)-5-(3-methyl-2-thienyl)-1-methyl-1,2,4-triazole (1.18 mmol., 364 mg) was dissolved in glacial acetic acid (4 ml). Bromine (2.36 mmol, 0.124 ml) was added in two portions and the reaction allowed to stir 5 days at room temperature. Diluted with water and extracted into diethyl ether, washed with saturated NaHCO3 and brine, dried over MgSO4. Concentrated to a white solid. Wgt. 0.51 g, recrystallized from hexane ethyl acetate to afford the product as a white solid (0.37 g, 81%) MP 117-118° C.; Anal. Calcd. For C14H10BrClFN3S; C, 43.44; H, 2.60; N, 10.86. Found; C, 43.46; H, 2.71; N, 10.81.

Workup

  1. extractionextracted into diethyl ether
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationConcentrated to a white solid
  5. custom0.51 g, recrystallized from hexane ethyl acetate

Sources & evidence

ORD record
ord-22a09e4015c84a5295422068d31c05bb
Source dataset
uspto-grants-2001_07
Patent number
US06265424B1

Reaction notes

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