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

HRID 1779739Notes

Reaction equation

HRID 1779739 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].[N:15]([O:17]CCC(C)C)=O.[ClH:23]>>[Cl:23][C:2]([CH3:14])([CH3:1])[CH:3]([N:15]=[O:17])[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 AcidHCID 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-nitrosopentane

Procedure

To a cooled (0°-5° C.) solution of 4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-pentene (4.0 g, 0.02 mol) (Example 11(A); synthesis is also described in U.S. patent application Ser. No. 08/054,120 recited above) in isoamyl nitrite (26 g, 30 mL, 0.22 mol) was added concentrated hydrochloric acid (3.5 mL, 0.035 mol) with stirring. The reaction mixture was maintained below 5° C. during the addition and stirred at 5° C. for an additional 2 hrs. The solid formed was filtered and washed with cold ether:ethanol (3:1, 150 mL) and dried. Yield: 5.0 g (96%). mp: 105°-107° C. 1H NMR (DMSO) ε 1.72 [s, 6H, C(CH3)2 ], 2.94 (t, 2H, CH2CH2N<), 4.65 (t, 2H, CH2CH2N<), 7.16 and 7.54 (s, 2H, imi H), 11.42 (s, 1H, NOH). MS: (M+H)+ =261.

Workup

  1. customsynthesis
  2. temperatureThe reaction mixture was maintained below 5° C. during the addition
  3. stirringstirred at 5° C. for an additional 2 hrs
  4. customThe solid formed
  5. filtrationwas filtered
  6. washwashed with cold ether:ethanol (3:1, 150 mL)
  7. customdried

Sources & evidence

ORD record
ord-cbdbd45f0c2640bd8edb6c9daebdbedf
Source dataset
uspto-grants-1997_05
Patent number
US05627286

Reaction notes

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