P,P-Diphenylphosphinic azide → 3-(4-(azidomethyl)phenyl)-1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazole

HRID 62069

Reaktionsgleichung

Reaktionsgleichung von HRID 62069
[F:1][C:2]([F:27])([O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[N:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25]O)=[CH:21][CH:20]=3)=[N:15]2)=[CH:10][CH:9]=1)[C:3]([F:6])([F:5])[F:4].C1(P([N:42]=[N+:43]=[N-:44])(C2C=CC=CC=2)=O)C=CC=CC=1.N1(C2CCCCCCCCCC2)CCCN=CCCCCC1>O1CCCC1.O.C(OCC)(=O)C>[N:42]([CH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:16]2[N:17]=[CH:18][N:14]([C:11]3[CH:12]=[CH:13][C:8]([O:7][C:2]([F:27])([F:1])[C:3]([F:6])([F:5])[F:4])=[CH:9][CH:10]=3)[N:15]=2)=[CH:20][CH:21]=1)=[N+:43]=[N-:44]

Komponenten

7

Edukt 3

HCID 199401P,P-Diphenylphosphinic azideHCID 118675138(4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)methanolHCID 1296629601,8-Diazabicycloundec-7ene

Produkt 1

HCID 1186751993-(4-(azidomethyl)phenyl)-1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazoleAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To (4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)methanol (2.00 g, 5.19 mmol) in tetrahydrofuran (25 mL) was added diphenylphosphoryl azide (1.30 g, 5.71 mmol), followed by dropwise addition of 1,8-diazabicycloundec-7-ene (0.861 mL, 5.71 mmol). The mixture was stirred at room temperature for 6 hours. The mixture was diluted with water and ethyl acetate. The organic phase was separated and rinsed with brine, dried over magnesium sulfate, and concentrated to provide the title compound as a yellow solid (1.85 g, 83%): ESIMS m/z 411 ([M+H]+).

Aufarbeitung

  1. customThe organic phase was separated
  2. washrinsed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-597a3af838d5477189c46bd9b8ecbee6
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09445594B2

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