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

HRID 278385ノート

反応式

HRID 278385 の反応式
[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

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 178430893HCID 178430893、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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 (CLCl3) 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)+.

後処理

  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

出典と根拠

ORDレコード
ord-50473f7953304bc3ac6749b42ce51f07
出典データセット
uspto-grants-2002_03
特許番号
US06359120B1

反応ノート

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