Hydrochloric Acid → 4-chloro-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-nitrosopentane

HRID 278393Notes

Reaction equation

HRID 278393 reaction equation
[CH3:1][C:2]([CH3:14])=[CH:3][CH2:4][CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[N+:11]([O-:13])=[O:12].[ClH:15].[N:16]([O:18]CCC(C)C)=O>>[Cl:15][C:2]([CH3:14])([CH3:1])[CH:3]([N:16]=[O:18])[CH2:4][CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid3×HCID 8053Isoamyl NitriteHCID 15186012N-(4-Methylpent-3-en-1-yl)-2-nitroimidazole

Product 1

HCID 151859944-chloro-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-nitrosopentaneYield 81%

Conditions

Temperature
0 °C

Procedure

4-Methyl-1-(2-nitro-1H-imidazol-1-yl)-3-pentene (8 g, 41 mmol) was dissolved in isoamyl nitrite (50 mL) at room temperature. The solution was cooled to 0° C. in an ice-salt bath and concentrated HCl (12 mL) was added dropwise. The reaction temperature was maintained between 3-5° C. during the HCl addition; the reaction was stirred in an ice-salt bath for 45 minutes after the addition of HCl. The product was filtered, washed with ethanol-ether (1:2) and dried in vacuum to give 8.6 g (81%) of the title product as a white solid; mp: 96-97° C. MS: (M+H)+=261, M+=260. 1H NMR (DMSO-d6) δ 1.70 (s, 6H, gem-di-CH3), 2.94 (t, 2H, CH2C=NOH), 4.65 [t, 2H, CH2-(2-nitroimidazole)], 7.16 and 7.52 (s, 2H, 2-nitroimidazolyl-H), 11.43 (s, 1H, CH2C=NOH).

Workup

  1. filtrationThe product was filtered
  2. washwashed with ethanol-ether (1:2)
  3. customdried in vacuum

Sources & evidence

ORD record
ord-37947bb49f624affb0eac929230b71e1
Source dataset
uspto-grants-2002_03
Patent number
US06359120B1

Reaction notes

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