Potassium Carbonate → Propyl 2-(2-methoxyphenyl)-3-phenyl-2-[(1,2,4-triazol-1-yl)methyl]-propionate

HRID 1608772Notes

Reaction equation

HRID 1608772 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([CH2:20][N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].I[CH2:33][CH2:34][CH3:35]>C(C(C)=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([CH2:20][N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:10]([O:12][CH2:33][CH2:34][CH3:35])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 200852002-(2-Methoxyphenyl)-3-phenyl-2-[(1,2,4-triazol-1-yl)methyl]propanoic acid

Product 1

HCID 20085202Propyl 2-(2-methoxyphenyl)-3-phenyl-2-[(1,2,4-triazol-1-yl)methyl]-propionateYield 82%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-(2-methoxyphenyl)-3-phenyl-2-[(1,2,4-triazol-1-yl)methyl]propanoic acid (6.0 g, 0.0178 mole) and potassium carbonate (3.6 g, 0.0213 mole) in methyl ethyl ketone (50 mL) was stirred and heated to reflux for 1 hour. Iodopropane (3.6 g, 0.0213 mole) was added and the mixture continued heating at reflux for an additional 4 hours and then allowed to cool to room temperature. The solvent was removed by distillation and 100 mL of water and 100 mL of ethyl acetate added. The organic phase was then separated, dried and concentrated on a rotary evaporator to afford 5.5 g of solid product (melting point 129°-130° C.; yield 82% ), Example 100 of Table 1.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperaturethe mixture continued heating
  4. temperatureat reflux for an additional 4 hours
  5. customThe solvent was removed by distillation and 100 mL of water and 100 mL of ethyl acetate
  6. additionadded
  7. customThe organic phase was then separated
  8. customdried
  9. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-2b11250b70fd48e89d64a5e519f9a324
Source dataset
uspto-grants-1995_03
Patent number
US05397768

Reaction notes

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