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Cesium carbonate → 4'-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2'-methyl-biphenyl-4-carboxylic acid methyl ester

HRID 424824
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 424824
Cl[CH2:2][C:3]1[N:7]([C:8]2[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:15])[N:6]=[N:5][C:4]=1[CH:16]([CH3:18])[CH3:17].[CH3:19][O:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:30]=2[CH3:36])=[CH:25][CH:24]=1)=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:19][O:20][C:21]([C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:2][C:3]3[N:7]([C:8]4[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=4[Cl:15])[N:6]=[N:5][C:4]=3[CH:16]([CH3:18])[CH3:17])=[CH:31][C:30]=2[CH3:36])=[CH:27][CH:28]=1)=[O:22]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 536647034'-Hydroxy-2'-methyl-biphenyl-4-carboxylic Acid Methyl EsterHCID 667041505-chloromethyl-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-[1,2,3]triazole

Produkt 1

HCID 667041164'-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2'-methyl-biphenyl-4-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a solution of 5-chloromethyl-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-[1,2,3]triazole (0.1 g, 0.328 mmol) in dimethylformamide (3 mL) is added 4′-hydroxy-2′methyl-biphenyl-4-carboxylic acid methyl ester (0.079 g, 0.326 mmol) and cesium carbonate (0.21 g, 0.646 mmol). The reaction is heated to 55° C. for 2.5 h and is cooled to room temperature. The reaction mixture is concentrated under reduced pressure. The residue is dissolved in 1N hydrochloric acid and ethyl acetate. The layers are separated and the aqueous is extracted again with ethyl acetate. The organic layers are combined and are washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give 4′-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2′-methyl-biphenyl-4-carboxylic acid methyl ester. ES/MS m/e (35Cl/37Cl) 510.2/512.2 (M+1).

Aufarbeitung

  1. temperatureis cooled to room temperature
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. dissolutionThe residue is dissolved in 1N hydrochloric acid
  4. customThe layers are separated
  5. extractionthe aqueous is extracted again with ethyl acetate
  6. washare washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c65f2a1aa3f54769b0fdea1e7d588d1e
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08106077B2

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