Diisopropylethylamine → N-(4-Methylpent-3-en-1-yl)-2-nitroimidazole

HRID 1779740Notes

Reaction equation

HRID 1779740 reaction equation
C(N(C(C)C)CC)(C)C.Cl[C:11]([CH3:26])([CH3:25])[CH:12](N=O)[CH2:13][CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[C:16]1[N+:20]([O-:22])=[O:21]>>[CH3:25][C:11]([CH3:26])=[CH:12][CH2:13][CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[C:16]1[N+:20]([O-:22])=[O:21]

Participants

3

Reactant 2

HCID 81531DiisopropylethylamineHCID 151859944-chloro-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-nitrosopentane

Product 1

HCID 15186012N-(4-Methylpent-3-en-1-yl)-2-nitroimidazole

Procedure

To a mixture of 7-amino-4-aza-3,3-dimethyl-5-oxaheptan-2-one oxime (Example 7(E), 0.875 g, 0.005 mol) and diisopropylethylamine (0.7 g, 0.0055 mol) was added 4-chloro-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-nitrosopentane (Example 10(A), 1.3 g, 0.05 mol) and the mixture was stirred at room temperature for 24 hrs. The white solid formed was filtered and dried. This was purified by column chromatography (silica gel, CH2Cl2 :CH3OH) followed by recrystallization from acetonitrile. mp 122°-123° C. 1H NMR (D2O)ε 1.16 [s, 6H, C(CH3)2 ], 1.36 [s, 6H, C(CH3)2 ], 1.81 (s, 3H, CH3), 2.87 (t, 2H, CH2CH2CN<), 3.11 (m, 2H, OCH2CH2NH), 3.86 (m, 2H,OCH2CH2NH), 4.69 (t, 2H, CH2CH2CN<), 7.10 and 7.36 (s, 2H, imiH). Anal. Calcd. for C16H29N7O5 : Found: C, 48.47; H, 7.39; N, 24.12. Calcd.: C, 48.11; H, 7.32; N, 24.55.

Workup

  1. customThe white solid formed
  2. filtrationwas filtered
  3. customdried
  4. customThis was purified by column chromatography (silica gel, CH2Cl2 :CH3OH)
  5. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-0dc69e8c21e14837ba92c23e01f7b6c6
Source dataset
uspto-grants-1997_05
Patent number
US05627286

Reaction notes

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