Cesium carbonate → 1-(4-chlorophenyl)-1H-imidazole-4-carbaldehyde

HRID 57429

Reaktionsgleichung

Reaktionsgleichung von HRID 57429
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[Cs+].[Cs+]>[NH4+].[Cl-].[Cu]I.CN(C=O)C>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:1]2[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]2)=[CH:11][CH:10]=1

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 125101-Chloro-4-iodobenzeneHCID 764281H-Imidazole-4-carbaldehydeHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Produkt 1

HCID 838830341-(4-chlorophenyl)-1H-imidazole-4-carbaldehydeAusbeute 107,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a mixture of 1H-imidazole-4-carbaldehyde (3.71 g, 38.6 mmol), 1-chloro-4-iodobenzene (13.81 g, 57.9 mmol), (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (1.10 g, 7.72 mmol), copper(I) iodide (0.368 g, 1.93 mmol) and cesium carbonate (25.2 g, 77 mmol) was added DMF (50 mL). The reaction was sealed and heated to 110° C. for 18 hours. The reaction mixture was then cooled to room temperature and diluted with a saturated solution of NH4Cl. A brown solid develops. Solid was collected, washed with water and air dried. Solid material was then dissolved in 10% MeOH:90% DCM solution and dried (Na2SO4), filtered and concentrated to afford a dark brown solid 1-(4-chlorophenyl)-1H-imidazole-4-carbaldehyde (8.55 g, 41.4 mmol, 107% yield). Material as used without further purification. LCMS m/z 207.1 (M+H)+, Rt 0.58 min.

Aufarbeitung

  1. customThe reaction was sealed
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. customSolid was collected
  4. washwashed with water and air
  5. customdried
  6. dissolutionSolid material was then dissolved in 10% MeOH
  7. dry with material90% DCM solution and dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3afaac30416d41f195407537c5aa6443
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434719B2

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