Diisopropylethylamine → 3,3,9,9-Tetramethyl-1-(4-methyl-2-nitro-1H-imidazol-1-yl)-4,8-diazaundecane-2,10-dione dioxime

Participants

Reaction Conditions

Reaction Steps

3-Chloro-3-methyl-2-nitroso-1-(4-methyl-2-nitro-1H-imidazol-1-yl)butane (3.41 g, 13.09 mmol) was added in portions to a stirred solution of N-(3-aminopropyl)-1-amino-1,1-dimethyl-2-butanone oxime (2.0 g, 11.56 mmol, Example 1) and (i-Pr)2NEt (1.64 g, 13.09 mmol) in dry acetonitrile (20 mL) at 50° C. under a nitrogen atmosphere. After the addition the reaction mixture was stirred for an additional 2 hours at 50° C. and cooled to room temperature. The solid which formed was filtered and recrystallized from acetonitrile to provide the title product as a light yellow colored solid. Yield: 3.08 g (59.4%); mp. 140-141° C.; 1H NMR (DMSO-d6) δ1.12 & 1.19[2s, 6H, C(CH3)2], 1.33(m, 2H, CH2CH2CH2), 1.70[s, 3H, C(═N)CH3], 1.79(bs, 2H, NH), 2.15(s, 3H, imi-CH3), 2,19(m, 4H, NHCH2), 5.19[s, 2H, NCH2C(═N)], 7.05(s, 1H, imi-CH) and 10.33 & 11.36(2s, 2H, NOH). Ms m/e 398 (M+H)+.

Provenance & Evidence