2-Butanamine, 2-methyl- → 3-Ethoxy-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione

Beteiligte Stoffe

Reaktionsschritte

To a room temperature solution of 4.9 g (29 mmol) of 3,4-diethoxy-3-cyclobutene-1,2-dione and 50 mL of THF was added 2.5 g (34 mmol) of 1,1-dimethyl-propylamine. After stirring at room temperature overnight, the reaction mixture was evaporated to a yellow oil. Trituration with Et2O and filtration gave 6.2 g (20 mmol, a 100% yield) of the title compound as a white solid: mp: 78-80° C.; 1H NMR: (300 MHz, DMSO-d6): δ 0.91 and 1.47 (t, J=7.5 Hz, 3H, rotamers), 1.36-1.97 (m, 6H), 4.70-4.92 (m, 2H), 5.41 and 5.99 (brs, 1H, rotamers); IR (KBr, cm-1H): 3252w, 3181w, 3067w, 2968m, 2887m, 1788m, 1695s, 1603s, 1578s, 1500-1434brs, 1343s; MS (CI) m/z (relative intensity): 212 (M+ +H, 100); Anal. Calcd. for C1OH15 NO3 : C 62.54; H 8.11; N 6.63. Found: C, 62.54; H, 8.12; N, 6.52.

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