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

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Reaction Steps

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.

Provenance & Evidence