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

HRID 874777Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 874777
[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

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 stifling 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. extractionwas then extracted twice with ethyl acetate
  3. washwhich was then washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter the drying agent was filtered off
  6. distillationthe solvent was distilled away under the reduced pressure
  7. customthe residue was then purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-34cfa072504f4aa7add2581f931f7795
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980937B2

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