4-Aminophenylacetonitrile → 5-(4-Amino-phenyl)-3-(2-fluoro-4-trifluoromethyl-phenyl)-3H-[1,2,3]triazol-4-ylamine

HRID 1639690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639690
CC(C)([O-])C.[K+].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][CH:9]=1.[N:17]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=1[F:30])=[N+:18]=[N-:19]>C(O)(C)(C)C>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[N:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:22][C:21]=3[F:30])[C:15]=2[NH2:16])=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 770004-AminophenylacetonitrileHCID 23665647Potassium tert-butoxideHCID 866450681-Azido-2-fluoro-4-(trifluoromethyl)benzene

Produkt 1

HCID 252156745-(4-Amino-phenyl)-3-(2-fluoro-4-trifluoromethyl-phenyl)-3H-[1,2,3]triazol-4-ylamineAusbeute 21,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To a stirred and ice-cooled solution of potassium tert-butoxide (1.728 g, 14.626 mmol) in tert-butanol (50 ml), commercial 4-aminophenylacetonitrile (1.418 g, 10.7258 mmol) and 1-azido-2-fluoro-4-trifluoromethyl-benzene (2.000 g, 9.7507 mmol) are added under a nitrogen atmosphere and the reaction mixture is allowed to attain spontaneously room temperature (1 h) and finally refluxed for 6 h. The resulting reaction mixture is concentrated, added water, and extracted with ethylacetate (3×100 ml). The combined organic layers are dried over MgSO4, filtered and evaporated, to afford a dark brown gummy material (3.289 g, 100% mass balance). The crude residue is purified by column chromatography over silica gel (230-400 mesh), eluting with 25% ethylacetate in petroleum ether, to obtain the title compound as a light yellow solid (0.700 g, 21% yield). M.p. 163.6-165.0° C. LC-ESI-HRMS of [M+H]+ shows 338.1021 Da. Calc. 338.102882 Da, dev. −2.3 ppm.

Aufarbeitung

  1. additionare added under a nitrogen atmosphere
  2. customto attain spontaneously room temperature
  3. custom(1 h)
  4. temperaturefinally refluxed for 6 h
  5. customThe resulting reaction mixture
  6. concentrationis concentrated
  7. additionadded water
  8. extractionextracted with ethylacetate (3×100 ml)
  9. dry with materialThe combined organic layers are dried over MgSO4
  10. filtrationfiltered
  11. customevaporated
  12. customto afford a dark brown gummy material (3.289 g, 100% mass balance)
  13. customThe crude residue is purified by column chromatography over silica gel (230-400 mesh)
  14. washeluting with 25% ethylacetate in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-46977813f8e74da48fab61a9890c8246
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110588B2

Notizen zur Reaktion

Wird geladen…