Triethylamine → 2-methyl-4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzoyl azide

HRID 59881

Reaktionsgleichung

Reaktionsgleichung von HRID 59881
[CH3:1][C:2]1[CH:10]=[C:9]([C:11]2[N:15]=[CH:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(N(CC)CC)C.P([N:50]=[N+:51]=[N-:52])(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1>C(O)(C)C>[CH3:1][C:2]1[CH:10]=[C:9]([C:11]2[N:15]=[CH:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:24])[F:25])=[CH:18][CH:17]=3)[N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([N:50]=[N+:51]=[N-:52])=[O:5]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 712093312-methyl-4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzoic acid

Produkt 1

HCID 866758162-methyl-4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzoyl azideAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To 2-methyl-4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzoic acid (0.412 g, 1.134 mmol) in a 100 mL round-bottomed flask equipped with a stir bar under N2 was added isopropyl alcohol (11 mL), triethylamine (0.205 ml, 1.474 mmol) and diphenyl phosphorazidate (0.319 ml, 1.474 mmol). The reaction was stirred at room temperature overnight. The resultant solid was filtered, washed with isopropyl alcohol followed by hexanes and dried under vacuum providing the title compound as a white solid (0.294 g, 0.757 mmol, 67%): 1H NMR (300 MHz, CDCl3) δ 8.60 (s, 1H), 8.13 (s, 1H), 8.11-8.02 (m, 2H), 7.84-7.77 (m, 2H), 7.40 (d, J=8.6 Hz, 2H), 2.74 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −58.02; ESIMS m/z 389 ([M+H]+).

Aufarbeitung

  1. filtrationThe resultant solid was filtered
  2. washwashed with isopropyl alcohol
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f0b0861a78864e13ac74a01537dd98cf
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440964B2

Verknüpfte Notizen

Wird geladen…