Acetic Acid → 1-{2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]phenyl}-1H-tetrazole

HRID 1930523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1930523
[Br:1][C:2]1[CH:8]=[C:7]([N:9]2[CH2:13][CH2:12][C:11]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[CH2:10]2)[CH:6]=[CH:5][C:3]=1[NH2:4].C(OCC)(OCC)OCC.[N-:36]=[N+:37]=[N-:38].[Na+].[C:40](O)(=O)C>O>[Br:1][C:2]1[CH:8]=[C:7]([N:9]2[CH2:13][CH2:12][C:11]([C:18]3[CH:19]=[C:20]([Cl:25])[CH:21]=[C:22]([Cl:24])[CH:23]=3)([C:14]([F:15])([F:16])[F:17])[CH2:10]2)[CH:6]=[CH:5][C:3]=1[N:4]1[CH:40]=[N:38][N:37]=[N:36]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 582188902-Bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]aniline

Produkt 1

HCID 582188931-{2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]phenyl}-1H-tetrazoleAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the mixture of 2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]aniline (0.60 g), triethyl orthoformate (0.98 g) and sodium azide (0.38 g) was added acetic acid (1.1 g), and the mixture was then heated with stirring at 100° C. for 4 hours. The mixture was cooled to room temperature and then poured into water, which was then extracted twice with ethyl acetate. The organic layer was combined, which was then washed with water and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was distilled away under the reduced pressure, and the residue was then purified by silica gel chromatography to yield 1-{2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]phenyl}-1H-tetrazole (0.52 g). m.p. 193-194° C.

Aufarbeitung

  1. temperaturethe mixture was then heated
  2. temperatureThe mixture was cooled to room temperature
  3. extractionwas then extracted twice with ethyl acetate
  4. washwhich was then washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter the drying agent was filtered off
  7. distillationthe solvent was distilled away under the reduced pressure
  8. customthe residue was then purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8d59b51b45b046799c73227056a633c2
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188122B2

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