4-(Trifluoromethoxy)phenylacetonitrile → 3-(2-Fluoro-4-trifluoromethyl-phenyl)-5-(4-trifluoromethoxy-phenyl)-3H-[1,2,3]triazol-4-ylamine

HRID 1639697Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639697
C[O-].[Na+].[F:4][C:5]([F:17])([F:16])[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]#[N:15])=[CH:9][CH:8]=1.[N:18]([C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=1[F:31])=[N+:19]=[N-:20]>CO>[F:31][C:22]1[CH:23]=[C:24]([C:27]([F:29])([F:30])[F:28])[CH:25]=[CH:26][C:21]=1[N:18]1[C:14]([NH2:15])=[C:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][C:5]([F:4])([F:16])[F:17])=[CH:12][CH:11]=2)[N:20]=[N:19]1

Komponenten

5

Edukt 3

HCID 1426764-(Trifluoromethoxy)phenylacetonitrileHCID 10942334Sodium MethoxideHCID 866450681-Azido-2-fluoro-4-(trifluoromethyl)benzene

Produkt 1

HCID 252159083-(2-Fluoro-4-trifluoromethyl-phenyl)-5-(4-trifluoromethoxy-phenyl)-3H-[1,2,3]triazol-4-ylamineAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred and ice-cooled solution of sodium methoxide (0.296 g, 5.4848 mmol) in methanol (25 ml), commercial 4-(trifluoromethoxy)phenylacetonitrile (0.809 g, 4.0222 mmol) and 1-azido-2-fluoro-4-trifluoromethyl-benzene (0.750 g, 3.6565 mmol) are added portion wise. The reaction mixture is allowed to reach room temperature spontaneously overnight, concentrated in vacuo, added water, and extracted with ethylacetate (3×80 ml). The combined organic layers are dried over MgSO4, filtered and evaporated, to afford a brown solid residue (1.385 g, 94% mass balance). This crude material is purified by column chromatography over silica gel (230-400 mesh) eluting with 9% ethylacetate in petroleum ether, to obtain the title compound as an off-white solid (0.490 g, 33% yield). M.p. 134.2-134.9° C. LC-ESI-HRMS of [M+H]+ shows 407.0747 Da. Calc. 407.074282 Da, dev. 1 ppm.

Aufarbeitung

  1. additionare added portion wise
  2. concentrationconcentrated in vacuo
  3. additionadded water
  4. extractionextracted with ethylacetate (3×80 ml)
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto afford a brown solid residue (1.385 g, 94% mass balance)
  9. customThis crude material is purified by column chromatography over silica gel (230-400 mesh)
  10. washeluting with 9% ethylacetate in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-15741e8eb4574a5aa449745cedc21f03
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110588B2

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