Chlorosuccinimide → Methyl 3-(5-chloro-2-methyl-1H-imidazol-4-yl)-4-methylbenzoate

HRID 1487846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1487846
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]1[NH:16][C:15]([CH3:17])=[N:14][CH:13]=1.C1C(=O)N([Cl:25])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Cl:25][C:13]1[NH:14][C:15]([CH3:17])=[N:16][C:12]=1[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[CH3:1])[C:6]([O:8][CH3:9])=[O:7]

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 90029434Methyl 4-methyl-3-(2-methyl-1H-imidazol-5-yl)benzoate2×

Produkt 1

HCID 90030158Methyl 3-(5-chloro-2-methyl-1H-imidazol-4-yl)-4-methylbenzoateAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of methyl 4-methyl-3-(2-methyl-1H-imidazol-5-yl)benzoate (compound 7.1, 317 mg, 1.38 mmol) in carbon tetrachloride (30 mL) was added NCS (184 mg, 1.38 mmol). The mixture was stirred at 50° C. for 16 hours, then cooled to room temperature and washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-50% EtOAc in hexanes) to yield the title compound as a solid (300 mg, 82%). m/z (ES+) 265 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 9.55 (br s, 1H), 8.01-7.87 (m, 2H), 7.37 (d, J=7.8 Hz, 1H), 3.91 (s, 3H), 2.42 (s, 3H), 2.40 (s, 3H).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (0-50% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c447fe4b4e78465189f50041ebc33696
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428502B2

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