Acetic Acid → 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenylmethanamine

HRID 62050

Reaktionsgleichung

Reaktionsgleichung von HRID 62050
[F:1][C:2]([F:34])([F:33])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:32]=[CH:31][C:18]([CH2:19][NH:20]C(=O)OCC4C=CC=CC=4)=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.C(O)(=O)C.C(OCC)C>Br>[F:34][C:2]([F:1])([F:33])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:32]=[CH:31][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=3)=[N:11]2)=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 90404490benzyl 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylcarbamate

Produkt 1

HCID 904040894-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenylmethanamineAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 260Hydrogen BromideLösungsmittel

Versuchsvorschrift

In a 200 mL flask, benzyl 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylcarbamate (0.599 g, 1.28 mmol) was suspended in hydrogen bromide in acetic acid (33 wt %, 8.00 mL, 45.7 mmol). The suspension was stirred vigorously at room temperature for 1 hour. To the resulting suspension was added diethyl ether (100 mL), and the reaction mixture was stirred for 30 minutes at room temperature. The resulting precipitate was collected via filtration and treated with sodium hydroxide (1 N) and extracted with ethyl acetate (3×75 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated to give the title compound as a white solid (0.395 g, 92% yield): 1H NMR (400 MHz, DMSO-d6) δ 9.45 (s, 1H), 8.25-8.03 (m, 4H), 7.74-7.62 (m, 2H), 7.60-7.48 (m, 2H), 3.85 (s, 2H); 19F NMR (376 MHz, DMSO-d6) δ −56.97; ESMIS m/z 318 ([M+H]+) (—NH2).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 30 minutes at room temperature
  2. filtrationThe resulting precipitate was collected via filtration
  3. additiontreated with sodium hydroxide (1 N)
  4. extractionextracted with ethyl acetate (3×75 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0b5a5f8c6c7b4850b4f33c03a3683cd8
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09445594B2

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