Butylamine → Butylamine

Participants

Reaction Steps

A standard solution of n-butylamine was prepared by adding 0.5 ml of n-butylamine to a 10 ml volumetric flask containing 10 ml dry methylene chloride. The n-butylamine solution (0.85 ml) was then added to 2-(1-benzotriazolyl)-5-ethyl-4H-3,1-benzoxazin-4-one (150 mg), prepared as described in Preparation VII above, in 21 mg of dry methylene chloride, and the mixture was stirred for 20 minutes. Analysis by TLC (20% ethyl acetate in toluene) indicated that the reaction was complete. The methylene chloride was then removed under reduced pressure and the remaining residue chromatographed over silica gel (10% ethyl acetate in toluene, flash column chromatography). All product fractions were combined and evaporated to give a solid that was recrystallized from pentane, yielding 40 mg of 2-n-butylamino-5-ethyl-4H-3,1-benzoxazin-4-one, m.p. 136°-137° C., IR, 330, 1725-1740 (broad), 1635, 1590, 1570 cm-1); 'H NMR(delta CDCl3): 1.0 (t, 3H, CH 3); 1.3 (t, 3H, CH3); 1.5 (m, 4H, CH2CH2); 3.2 (q, 2H, PhCH2); 3.4 (q, 2H, CH2NH); 4.8 (broad, s, 1H, NH); 6.9-7.6 (m, 3H, ArH).

Provenance & Evidence