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

HRID 2293898노트

반응식

HRID 2293898 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-80c87bd6374145479fd6e4d664df8fc2
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05688487

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