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

HRID 1984741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984741
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:20][C:21]1[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24]>ClCCl.O>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:23]([C:22]1[CH:26]=[CH:27][CH:28]=[C:29]([CH3:30])[C:21]=1[CH3:20])=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 779181-BenzylimidazoleHCID 28008992,3-Dimethylbenzoyl chloride

Produkt 1

HCID 66771502(1-Benzyl-1H-imidazol-2-yl)(2,3-dimethylphenyl)methanoneAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1-benzyl-1H-imidazole (1.69 Kg, 10.56 mol) in dichloromethane (14.0 L), at −7° C., was added triethylamine (1.61 kg, 10.56 mol). A solution of 2,3-dimethylbenzoyl chloride (2.0 kg, 11.99 mol) in dichloromethane (6.0 L) was then added dropwise and the reaction mixture was stirred at room temperature for 16 h. The reaction was monitored by Thin layer Chromatography. After completion of the reaction, the reaction mixture was diluted with water (5.0 L) and the mixture was stirred for a further 15 min. The two layers were separated and the organic phase was concentrated in vacuo. To the residue was added toluene (8.0 L) and the solution was cooled to −5° C., before addition of hydrochloric acid (5N, 8.0 L). The two layers were separated and the aqueous layer was adjusted to pH 9-12, by addition of aqueous sodium hydroxide solution (50%), and extracted with toluene (4.0 L and then 8.0 L). The combined organic phases were concentrated in vacuo to give the title compound (2.8 kg).

Aufarbeitung

  1. customAfter completion of the reaction
  2. stirringthe mixture was stirred for a further 15 min
  3. customThe two layers were separated
  4. concentrationthe organic phase was concentrated in vacuo
  5. additionTo the residue was added toluene (8.0 L)
  6. temperaturethe solution was cooled to −5° C., before addition of hydrochloric acid (5N, 8.0 L)
  7. customThe two layers were separated
  8. additionthe aqueous layer was adjusted to pH 9-12, by addition of aqueous sodium hydroxide solution (50%)
  9. extractionextracted with toluene (4.0 L
  10. concentrationThe combined organic phases were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e3a7b55edf4140dcb569a86fb3fd9d02
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544706B2

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