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Acetonitrile → 4-[({4-[3-(2,6-dichlorophenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methylphenyl}-methylamino)-methyl]-2-methyl-benzoic acid methyl ester

HRID 424847
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 424847
BrC[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[C:16]([F:19])([F:18])[F:17].O[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][CH2:29][C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[C:32]([CH3:40])[CH:31]=2)=[C:23](C)[CH:22]=1.[C:42](=[O:45])([O-])[O-].[K+].[K+].[C:48](#N)C>>[CH3:37][O:36][C:34](=[O:35])[C:33]1[CH:38]=[CH:39][C:30]([CH2:29][N:28]([C:27]2[CH:22]=[CH:21][C:26]([O:45][CH2:42][C:3]3[N:7]([C:8]4[C:9]([Cl:15])=[CH:10][CH:11]=[CH:12][C:13]=4[Cl:14])[N:6]=[N:5][C:4]=3[C:16]([F:18])([F:17])[F:19])=[CH:25][C:24]=2[CH3:23])[CH3:48])=[CH:31][C:32]=1[CH3:40]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 667042144-{[(4-Hydroxy-2-methylphenyl)methylamino]methyl}-2-methyl benzoic acid, methyl esterHCID 866292535-bromomethyl-1-(2,6-dichlorophenyl)-4-trifluoromethyl-1H-triazole

Produkt 1

HCID 66704211
4-[({4-[3-(2,6-dichlorophenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methylphenyl}-methylamino)-methyl]-2-methyl-benzoic acid methyl ester
Ausbeute 97 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 5-bromomethyl-1-(2,6-dichlorophenyl)-4-trifluoromethyl-1H-triazole (15.65 g, 41.7 mmol) and 4-{[(4-hydroxy-2-methylphenyl)methylamino]methyl}-2-methyl benzoic acid, methyl ester (12.49 g, 41.7 mmol) in acetonitrile (120 mL) is added potassium carbonate (11.54 g, 83.4 mmol) at room temperature. The mixture is heated at 90° C. overnight. After 16 h, the reaction is cooled to room temperature and filtered through a pad of diatomaceous earth. The solvent is removed under reduced pressure. The residue is diluted with MTBE and washed with 2N NaOH, water, and brine. The organic layer is dried over magnesium sulfate, filtered, and evaporated to afford 4-[({4-[3-(2,6-dichlorophenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methylphenyl}-methylamino)-methyl]-2-methyl-benzoic acid methyl ester (24.2 g, 97%). ES/MS m/e 593 (M+1).

Aufarbeitung

  1. temperaturethe reaction is cooled to room temperature
  2. filtrationfiltered through a pad of diatomaceous earth
  3. customThe solvent is removed under reduced pressure
  4. additionThe residue is diluted with MTBE
  5. washwashed with 2N NaOH, water, and brine
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-56d5636957a0466dba4866b95eba94c6
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08106077B2

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