The reaction of isatoic anhydride (1) with methylhydrazine in dimethylformamide at 45-50 "C yielded predominantly I-(0-aminobenzoy1)-1-methylhydrazine (2), whose structure was confirmed by conversion to the known 3,4dihydro-4-methyl-1H-1,3,4-benzotriazepine-2,5-dione (4) with ethyl chloroformate. Hydrazide 2 was treated with triethyl ortho esters to produce 2-substituted 3,4-dihydro-4-methyl-5H-1,3,4-benzotriazepin-5-ones 5a-d.

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N-Phenyl-3,5-bis(methylthio )isothiazolecarboxamide ( 19).-A mixture of 0.75 g. (0.003 mole) of 16, 1.75 g. (0.019 mole) of aniline, and 100 ml. of ethyl ether was heated under reflux for 15 min., then was diluted with water and methylene chloride. The organic phase was washed with dilute hydrochloric acid and water. Evaporation and recrystallization from methanol gave 0.69 g. (82% yield) of the anilide, m.p. 162-163°; 287 m/¿ (e 13,300), 255 (16,500).Anoí. Caled, for C12H12ON2S3: C, 48.6; , 4.1. Found: C, 48.7; H, 4.3.N-(o-Aminophenyl)-3,5-dimethylthio-4-isothiazolecarboxamide ( 20).-To a solution of 2.7 g. (0.025 mole) of o-phenylenediamine and 2.5 g. (0.025 mole) of triethylamine in 75 ml. of tetrahydrofuran was added 6.24 g. (0.025 mole) of 16 in 130 ml. of tetrahydrofuran over 15 min. at room temperature. The mixture was stirred 1 hr., filtered, evaporated to dryness, and triturated with a little methanol to give 6.8 g. (87%) of a solid that melted at 179-180°. A sample recrystallized from a benzene-methanol mixture melted at 182.5-183°;287 (e 12,300), 233 (10,100).

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