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Triethylamine → (1-Benzyl-1H-imidazol-2-yl)(2-bromo-3-methylphenyl)methanone

HRID 734479
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 734479
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[CH2:16]([N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>C(#N)C>[CH2:16]([N:23]1[CH:27]=[CH:26][N:25]=[C:24]1[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:2]=1[Br:1])=[O:6])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 779181-BenzylimidazoleHCID 27355882-Bromo-3-methylbenzoic acid

Produkt 1

HCID 66771155(1-Benzyl-1H-imidazol-2-yl)(2-bromo-3-methylphenyl)methanoneAusbeute 102,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 2-bromo-3-methylbenzoic acid (2.0 g, 9.3 mmol) in thionyl chloride (4.75 ml, 65.1 mmol) was heated at 65° C., under nitrogen, for 3 h. The mixture was concentrated in vacuo and to the residue was added acetonitrile (25 ml). This solution was concentrated in vacuo and the process was repeated. To the final residue was added acetonitrile (25 ml), 1-benzylimidazole (1.62 g, 10.2 mmol) and triethylamine (1.44 ml, 10.2 mmol) and the reaction mixture was heated at 60° C., under nitrogen, for 18 h. The mixture was concentrated in vacuo and to the residue was added ethyl acetate (80 ml). The solution was washed with water (40 ml) and saturated aqueous sodium hydrogen carbonate solution (40 ml), dried (MgSO4) and concentrated in vacuo to give the title compound (3.38 g).

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo and to the residue
  2. additionwas added acetonitrile (25 ml)
  3. concentrationThis solution was concentrated in vacuo
  4. concentrationThe mixture was concentrated in vacuo and to the residue
  5. additionwas added ethyl acetate (80 ml)
  6. washThe solution was washed with water (40 ml) and saturated aqueous sodium hydrogen carbonate solution (40 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b3e311d636bc4019bca38db43e9304ee
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07592362B2

Notizen zur Reaktion

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