594 Journal of Medicinal Chemistry, 1979, Vol. 22, No.5 of acetone was added, and, after cooling the solution to -5 "C, 15 drops of Et,N were added with stirring and the mixture was kept a t 4 "C for 24 h. It was then evaporated to a syrup and 100 mL of benzene was added; after reducing the volume to 10 mL, the solution was applied to a dry silica gel column (3 x 100 cm), and the product was eluted with a mixture of benzene-acetone (91): yield 855 mg (13%);mp 117-121 "C dec; MS mle 131 (M+); UV A, (pH 7.0) 307 nm (c 7729); A, (pH 6.0) 272 nm ( t 5947), 308 ( e 3144) sh; Amax (pH 5.0) 270 nm (c 7729). 5-Methyl-1,3-oxazine-2,6(3H)-dione. A. 3-Ethoxycarbonylamino-2-methylacrylic acid18 (17.3 g) was added to hot (75-80 "C) polyphosphoric acid (170 g, 82-84% Pz05)with stirring. The mixture was stirred at 75-80 "C for a total of 45 min, poured into 100 mL of ice-water, and stirred to a smooth slurry. The precipitate was filtered, washed with cold water, and dried over Pz05: yield 8.5 g; mp 129-131 "C. The product was recrystallized from ethyl acetate: yield 6.2 g (56%);mp 134-135.5 "C; UV A, (EtOH) 271 nm (c 6500); NMR (MezSO-d8)6 1.83 (d, 3, JCHb4 = 1.5 Hz), 7.56 (q, 1, J4
