Potassium Carbonate → 1-(4-methyl-2-nitro-1H-imidazol-1-yl)-3-methyl-2-butene

HRID 2293898Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2293898
[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4]Br.C([O-])([O-])=O.[K+].[K+].[CH3:13][C:14]1[N:15]=[C:16]([N+:19]([O-:21])=[O:20])[NH:17][CH:18]=1>CC(C)=O>[CH3:13][C:14]1[N:15]=[C:16]([N+:19]([O-:21])=[O:20])[N:17]([CH2:4][CH:3]=[C:2]([CH3:6])[CH3:1])[CH:18]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 178430893HCID 178430893, Verbindung

Produkt 1

HCID 151860141-(4-methyl-2-nitro-1H-imidazol-1-yl)-3-methyl-2-butene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

3,3-Dimethylallyl bromide (14.08 g, 94.49 mmol) was added to a suspension of anhydrous K2CO3 (13.0 g, 94.20 mmol) and 4-methyl-2-nitroimidazole (10.0 g, 78.74 mmol, D. P. Davies et al, J. Heterocyclic Chem., 1982, 19, 253-256) in dry acetone (100 mL). The reaction mixture was stirred at room temperature under nitrogen atmosphere for 15 hours. The insoluble inorganic material was removed by filtration and the filtrate was evaporated to afford a brown paste which was loaded onto a silica gel column and eluted with hexane ethyl acetate (8.5:1.5). The fractions containing the compound with Rf 0.51 (silica gel TLC, hexane-ethyl acetate, 7:3) were collected and evaporated to afford a solid which was recrystallized from ethyl acetate-hexane to provide 1-(4-methyl-2-nitro-1H-imidazol-1-yl)-3-methyl-2-butene as a light yellow crystalline solid in 60% (9.21 g) yield; mp. 53°--54° C; 1H NMR (CDCl3) δ 1.80 [s, 6H, C(CH3)2 ], 2.26 (s, 3H, imi-CH3), 4.97 (d, 2H, J=7.26 Hz, NCH2), 5.36 (t, 1H, J=7.26 Hz, CH2CH) and 6.90 (s, 1H, imi-CH). 13C NMR (CDCl3) δ 13.80 (imi-CH3), 18.16 & 25.70 [C(CH3)2 ], 47.76 (NCH2), 117.35 (CH2CH), 122.77 (imi-CH), 138.09 [C(CH3)2 ], 139.97 (imi-CCH3) and 143.53 (CNO2). MS m/e 196 (M+H)+.

Aufarbeitung

  1. customThe insoluble inorganic material was removed by filtration
  2. customthe filtrate was evaporated
  3. customto afford a brown paste which
  4. washeluted with hexane ethyl acetate (8.5:1.5)
  5. additionThe fractions containing the compound with Rf 0.51 (silica gel TLC, hexane-ethyl acetate, 7:3)
  6. customwere collected
  7. customevaporated
  8. customto afford a solid which
  9. customwas recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-80c87bd6374145479fd6e4d664df8fc2
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05688487

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