Triethylamine → HCID 66770931, compound

HRID 1169979Notes

Reaction equation

HRID 1169979 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=O)=[O:4].S(Cl)(Cl)=O.[CH2:18]([N:25]1[CH:29]=[CH:28][N:27]=[CH:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>C(#N)C>[CH2:18]([N:25]1[CH:29]=[CH:28][N:27]=[C:26]1[C:8]([C:7]1[CH:6]=[C:5]([CH:13]=[CH:12][CH:11]=1)[C:3]([O:2][CH3:1])=[O:4])=[O:10])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 779181-BenzylimidazoleHCID 6018803-(Methoxycarbonyl)benzoic acid

Product 1

HCID 66770931HCID 66770931, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-(methoxycarbonyl)benzoic acid (2.53 g, 14.0 mmol) in thionyl chloride (7.17 ml, 98.30 mmol) was heated at reflux for 1 h. The mixture was cooled and concentrated in vacuo and to the residue was added toluene. This solution was concentrated in vacuo and to the residue was added anhydrous acetonitrile (24 ml), 1-benzyl-1H-imidazole (2.22 g, 14.0 mmol) and triethylamine (2.35 ml, 16.9 mmol). The reaction mixture was heated at reflux for 18 h and then cooled and concentrated in vacuo. To the residue was added ethyl acetate and the solution was washed with water and saturated aqueous sodium hydrogen carbonate solution. The organic phase was filtered through silica, eluting with ethyl acetate, and the filtrate was concentrated in vacuo to give the title compound (3.82 g).

Workup

  1. temperatureat reflux for 1 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo and to the residue
  4. additionwas added toluene
  5. concentrationThis solution was concentrated in vacuo and to the residue
  6. temperatureThe reaction mixture was heated
  7. temperatureat reflux for 18 h
  8. temperaturecooled
  9. concentrationconcentrated in vacuo
  10. additionTo the residue was added ethyl acetate
  11. washthe solution was washed with water and saturated aqueous sodium hydrogen carbonate solution
  12. filtrationThe organic phase was filtered through silica
  13. washeluting with ethyl acetate
  14. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c5ac97df02df479dad674381c0f2fda1
Source dataset
uspto-grants-2010_11
Patent number
US07825149B2

Reaction notes

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