Triethylamine → (1-Benzyl-1H-imidazol-2-yl)(2,3-dimethylphenyl)methanone

HRID 734469

Reaktionsgleichung

Reaktionsgleichung von HRID 734469
[CH3:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:12]([N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>S(Cl)(Cl)=O.C(#N)C>[CH2:12]([N:19]1[CH:23]=[CH:22][N:21]=[C:20]1[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:2]=1[CH3:1])=[O:6])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 117822,3-Dimethylbenzoic acidHCID 779181-Benzylimidazole

Produkt 1

HCID 66771502(1-Benzyl-1H-imidazol-2-yl)(2,3-dimethylphenyl)methanoneAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

A solution of 2,3-dimethylbenzoic acid (100 g, 666 mmol) in thionyl chloride (350 ml) was heated at 80° C. for 1 h, before cooling to room temperature and concentrating in vacuo. To the residue was added toluene (100 ml) and the solution was again concentrated in vacuo. The intermediate acid chloride was added to a mixture of 1-benzylimidazole (100 g, 632 mmol) and triethylamine (100 ml) in acetonitrile (1 l) and the reaction mixture was heated at reflux for 18 h. The reaction mixture was concentrated in vacuo and to the residue was added diethyl ether (500 ml) and ethyl acetate (50 ml). This solution was washed with water (500 ml) and saturated aqueous sodium hydrogen carbonate solution (500 ml), filtered through silica gel (100 g) and concentrated in vacuo to give the title compound (182 g).

Aufarbeitung

  1. concentrationconcentrating in vacuo
  2. additionTo the residue was added toluene (100 ml)
  3. concentrationthe solution was again concentrated in vacuo
  4. temperaturethe reaction mixture was heated
  5. temperatureat reflux for 18 h
  6. concentrationThe reaction mixture was concentrated in vacuo and to the residue
  7. additionwas added diethyl ether (500 ml) and ethyl acetate (50 ml)
  8. washThis solution was washed with water (500 ml) and saturated aqueous sodium hydrogen carbonate solution (500 ml)
  9. filtrationfiltered through silica gel (100 g)
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e89f9e2752554aa7898539246a8cfbb8
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592362B2

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