Potassium Iodide → HCID 59354903, compound

HRID 1099464Notes

Reaction equation

HRID 1099464 reaction equation
[CH3:1][C:2]1[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4][NH:5][N:6]=1.Br[CH2:13][CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C.O>[CH2:13]([N:5]1[N:4]=[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]([CH3:1])=[N:6]1)[CH:14]([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 78046Ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate

Product 1

HCID 59354903HCID 59354903, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To av solution of ethyl 5-methyl-2H-1,2,3-triazole-4-carboxylate (0.5 g, 3.2 mmol) in acetonitrile (40 mL) were added 1-bromo-2-methylpropane (1.25 mL, 11.5 mmol), potassium carbonate (2.66 g, 19.2 mmol) and a catalytic amount of potassium iodide. The reaction mixture was heated to 60° C. for 22 h. The reaction mixture was allowed to cool to ambient temperature and was diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to yield 293 mg (43%) of the title compound; MS (APPI/APCI) m/z 212[M+H+].

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98ad81567f534bc9b361991a0a1d41c8
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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