Toluene-p-sulphonic anhydride → 2-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl 4-methylbenzenesulfonate

HRID 1011456Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1011456
[N+:1]([C:4]1[N:5]([CH2:9][C:10]2[N:11]=[N:12][N:13]([CH2:15][CH2:16][OH:17])[CH:14]=2)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[O:18](S(C1C=CC(C)=CC=1)(=O)=O)[S:19]([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=O)=[O:20]>C(Cl)Cl>[CH3:26][C:25]1[CH:27]=[CH:28][C:22]([S:19]([O:17][CH2:16][CH2:15][N:13]2[CH:14]=[C:10]([CH2:9][N:5]3[CH:6]=[CH:7][N:8]=[C:4]3[N+:1]([O-:3])=[O:2])[N:11]=[N:12]2)(=[O:20])=[O:18])=[CH:23][CH:24]=1

Komponenten

4

Edukt 2

HCID 77773Toluene-p-sulphonic anhydrideHCID 575402032-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethanol

Produkt 1

HCID 595110572-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl 4-methylbenzenesulfonateAusbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a round bottom flask containing alcohol 11 (160 mg, 0.672 mmol), TEA (136 mg, 1.34 mmol) and DCM (5 mL) was added Ts2O (263 mg, 0.806 mmol). The reaction was stirred at RT for 4 hrs. TLC indicated that the reaction was complete. The reaction was concentrated in vacuo and purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford 140 mg (53% yield) of 12 as a pale orange oil. Mass Spec (lo-res): Calc'd for C15H16N6O5S: 392.092; found: 393.10 (M+H).

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified on a silica gel cartridge

Quellen und Nachweise

ORD-Eintrag
ord-20b5fae0eae44ddc852e1d66daddc2d0
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977361B2

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