Benzyl azide → ethyl 2-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylate

HRID 2381804Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2381804
[C:1]([C:3]1[S:4][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([CH3:8])[N:7]=1)#[CH:2].C(N(CC)C(C)C)(C)C.[CH2:23]([N:30]=[N+:31]=[N-:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1.[Cu]I>[CH2:23]([N:30]1[CH:2]=[C:1]([C:3]2[S:4][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([CH3:8])[N:7]=2)[N:32]=[N:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

6

Edukt 3

HCID 12152Benzyl azideHCID 81531DiisopropylethylamineHCID 59179676Ethyl 2-ethynyl-4-methylthiazole-5-carboxylate

Produkt 1

HCID 59179723ethyl 2-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylateAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-ethynyl-4-methylthiazole-5-carboxylate (0.19 g, 0.71 mmol) in tetrahydrofuran (5 mLl) was added copper(I) iodide (0.003 g, 0.014 mmol), N,N-diisopropylethylamine (0.15 mL, 0.74 mmol) and benzylazide (0.11 g, 0.85 mmol). The reaction mixture was stirred at ambient temperature for 17 hours and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate:hexanes, 1:1) to afford the title compound as a yellow solid (0.23 g, 98%): 1H NMR (300 MHz, CDCl3) δ 7.98 (s, 1H), 7.39-7.26 (m, 5H), 5.54 (s, 2H), 4.30 (q, J=7.1 Hz, 2H), 2.67 (s, 3H), 1.21 (t, J=7.1 Hz, 3H); MS (ES+) m/z 329.3 (M+1).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (ethyl acetate:hexanes, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-cc24de3180804effa0a3d660079baf37
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258160B2

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