Potassium Carbonate → HCID 118343997, compound

HRID 1753103Notes

Reaction equation

HRID 1753103 reaction equation
[C:1]([C:5]1[N:9]=[C:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:17][CH2:18][O:19][CH3:20].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][C:8]1[N:7]([CH2:17][CH2:18][O:19][CH3:20])[N:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[N:9]=1)[CH3:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 118344011HCID 118344011, compound

Product 1

HCID 118343997HCID 118343997, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

Ethyl (3-tert-Butyl-1H-1,2,4-triazol-5-yl)acetate (Preparation 116, 27.4 g, 0.13 mol) and 1-bromo-2-methoxyethane (13.7 mL, 0.143 mol) was dissolved in DMF (400 mL). K2CO3 (90.0 g, 0.65 mol) was added and the reaction mixture was stirred for 6 hours at 50-60° C. The reaction was cooled to room temperature, diluted with water (400 mL), and extracted with Et2O (3×100 mL). The combined organic extracts were washed with brine (3×200 mL), dried with Na2SO4, and evaporated to afford a mixture of alkylated triazole residues. The mixture was separated using HPLC (Luna 10 u 018(2), 100 A, 21.2×250 mm, H2O/acetonitrile 30-40%) to afford ethyl[3-tert-Butyl-1-(2-methoxyethyl)-1H-1,2,4-triazol-5-yl]acetate (23.14 g, 66%).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with Et2O (3×100 mL)
  3. washThe combined organic extracts were washed with brine (3×200 mL)
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customto afford
  7. customThe mixture was separated

Sources & evidence

ORD record
ord-746ce31041474ec0beb0c4af897c9cce
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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