Hydrochloric Acid → 3-Chloro-3-methyl-2-nitroso-1-(5-methyl-2-nitro-1H-imidazol-1-yl)butane

HRID 2293901Notes

Reaction equation

[CH3:1][C:2]1[N:6]([CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[C:5]([N+:12]([O-:14])=[O:13])=[N:4][CH:3]=1.[N:15]([O:17]CCC(C)C)=O.[ClH:23]>>[Cl:23][C:9]([CH3:11])([CH3:10])[CH:8]([N:15]=[O:17])[CH2:7][N:6]1[C:2]([CH3:1])=[CH:3][N:4]=[C:5]1[N+:12]([O-:14])=[O:13]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 8053Isoamyl Nitrite

HCID 151860151-(5-methyl-2-nitro-1H-imidazol-1-yl)-3-methyl-2-butene

Product 1

HCID 151860173-Chloro-3-methyl-2-nitroso-1-(5-methyl-2-nitro-1H-imidazol-1-yl)butaneYield 60%

Procedure

3-Chloro-3-methyl-2-nitroso-1-(5-methyl-2-nitro-1H-imidazol-1-yl)butane was prepared in 60% yield from 1-(5-methyl-2-nitro-1H-imidazol-1-yl)-3-methyl-2-butene (1.0 g, 5.12 mmol, Example 27), isoamyl nitrite (5.0 mL) and concentrated HCl (5.0 mL) following the procedure described for the preparation of its positional isomer (Example 27B) as a light blue solid; mp. 102°-105° C. (decomp); 1H NMR (DMSO-d6) δ 1.73 [s, 6H, C(CH3)2 ], 2.32 (s, 3H, imi-CH3), 5.53 (s, 2H, NCH2), 6.97 (s, 1H, imi-CH) and 11.58 (s, 1H, NOH). MS m/e 261 (M+H)+.

Workup

customdescribed for the preparation of its positional isomer (Example 27B) as a light blue solid

Sources & evidence

ORD record: ord-942b1fd0ec1c457aa1de94be68824eb9
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688487

Reaction notes

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