4-Acetamidophenylacetonitrile → N-{4-[5-Amino-1-(2-fluoro-4-trifluoromethyl-phenyl)-1H-[1,2,3]triazol-4-yl]-phenyl}-acetamide

HRID 1639689

Reaktionsgleichung

Reaktionsgleichung von HRID 1639689
CC(C)([O-])C.[K+].[C:7]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]#[N:19])=[CH:13][CH:12]=1)(=[O:9])[CH3:8].[N:20]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][C:24]=1[F:33])=[N+:21]=[N-:22]>C(O)(C)(C)C>[NH2:19][C:18]1[N:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][C:24]=2[F:33])[N:21]=[N:22][C:17]=1[C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:7](=[O:9])[CH3:8])=[CH:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 2897484-AcetamidophenylacetonitrileHCID 23665647Potassium tert-butoxideHCID 866450681-Azido-2-fluoro-4-(trifluoromethyl)benzene

Produkt 1

HCID 25215673N-{4-[5-Amino-1-(2-fluoro-4-trifluoromethyl-phenyl)-1H-[1,2,3]triazol-4-yl]-phenyl}-acetamideAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To a stirred and ice-cooled solution of potassium tert-butoxide (0.432 g, 3.6566 mmol) in tert-butanol (15 ml), commercial 4-acetamidophenylacetonitrile (0.5096 g, 2.9252 mmol) and 1-azido-2-fluoro-4-trifluoromethyl-benzene (0.500 g, 2.4377 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 (0.900 g, 97% mass balance). The crude residue is purified by column chromatography over silica gel (230-400 mesh), eluting with 50% ethylacetate in petroleum ether, to obtain the title compound as a light yellow solid (0.270 g, 30% yield). M.p. 114.8-116.2° C. LC-ESI-HRMS of [M+H]+ shows 380.1125 Da. Calc. 380.113447 Da, dev. −2.5 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 (0.900 g, 97% mass balance)
  13. customThe crude residue is purified by column chromatography over silica gel (230-400 mesh)
  14. washeluting with 50% ethylacetate in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-672e0e29244b4ddfa2debdbdddcf354f
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110588B2

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