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United States Patent Office Patented Nov 3,355,453 United States Patent Office Patented Nov. 28, 1967 1. 2 3,355,453 hydrogen chloride split off by the reaction, the amount of N-SUBSTITUTED BENZO-1,3-OXAZINE acid-binding agent present in the reaction mixture being at least one molar equivalent of the amount of chloro Klaus Hasspacher, BiberachDIGNE-(2,4) an der Riss, Germany, assigsb formic acid ester used as the starting material. Examples or, by messae assignments, to Boehringer Ingelhein of suitable acid-binding agents are inorganic bases, such G.m.b.H., Ingelheim am Rhein, Germany, a corpora tion of Germany as alkali metal hydroxides, alkali metal carbonates and No Drawing. Fied May 24, 1963, Ser. No. 282,887 the like, or tertiary organic bases, such as triethylamine, Claims priority, applicationa Germany, May 25, 1960, tributylamine, pyridine, N-methyl-piperidine and the like. T 18,445 The reaction is further advantageously performed in the 10 presence of an inert organic solvent, such as benzene, 12 Ciaims. (C. 269-244) toluene, tetrahydrofuran, dioxane and the like. These This is a continuation-in-part of copending applica inert organic solvents may also be present in the form of tion Ser. No. 111,926, filed May 23, 1961. mixtures with water, which is especially useful when an This invention relates to N-substituted benzo-1,3-ox inorganic base is used as the acid-binding agent. azine-diones-(2,4) and to various methods of preparing 5 The mixed anhydride Va obtained in the manner de these compounds. scribed above does not need to be isolated, but may in More particularly, the present invention relates to N stead be directly reacted with an amine of the Formula substituted benzo-1,3-oxazine-diones-(2,4) of the formula VI in the presence of one of the above mentioned solvents. R2 This reaction is advantageously performed at room tem 20 perature and is carried to completion at moderately ele R3 vated temperatures. Method B-By reacting an o-hydroxy-carboxylic acid Ri-- carbonate compound of the formula O . R (I) 25 COOH wherein: R1 R and R2, which may be identical to or different from O-COORs each other, are selected from the group consisting of (IV) chlorine and bromine, wherein R1 has the same meanings as defined above in R is selected from the group consisting of hydrogen, 30 connection with Formula I and Rs has the same meanings chlorine and bromine, and as defined above in connection with Formula III, either R is selected from the group consisting of hydrogen, with an equimolar amount of a chloroformic acid ester chlorine, bromine and nitro. of the Formula II above or with a halogenating agent, The compounds of the present invention may be pre such as a thionyl halide, a sulfuryl halide or a phosphorus pared by a variety of methods, but the following have 35 halide, to form a mixed anhydride of the formula proved to be most convenient and efficient: Method A-By reacting one mol of an aromatic o CO-X hydroxy-carboxylic acid of the formula R1 O-COORs 40 COO O (Vb) R1 wherein X is either halogen or -OCOOR, R and Rs O having the meanings previously defined, and then react (II) ing the mixed anhydride Vb with an amine of the formula wherein R1 has the same meanings as defined above in connection with Formula I, with at least two mols of a chloroformic acid ester of the formula HN - X C1-COORs (III) R (VI) wherein R5 is selected from the group consisting of lower wherein R2, R3 and R4 have the meanings previously de alkyl, aralkyl and aryl, to form a mixed anhydride of the 50 fined in connection with Formula I. formula The reaction of carbonate compound IV with the chloroformic acid ester III is carried out in the same COO-COORs manner and under the same conditions as described in R1 Method A. 55 However, the reaction of carbonate compound IV R}-o-coor: (Va) with the halogenating agent is performed at elevated wherein R1 and Rs have the meanings previously defined, temperatures, preferably at the boiling point of the halo and then reacting the mixed anhydride Va with an amine genating agent, and advantageously with a stoichiometric of the formula excess of the halogenating agent. If desired, this reaction 60 may also be performed in the presence of an inert solvent. R2 The unreacted excess of halogenating agent is distilled off in vacuo after completion of the reaction. The mixed anhydride Vb obtained in the manner de Rg (VI) scribed above does not need to be isolated, but may in 65 stead be directly reacted with an amine of the Formula wherein R2, R and R4 have the meanings previously de VI in the presence of one of the above mentioned sol fined in connection with Formula I. vents. This reaction is advantageously performed at room The reaction of the aromatic o-hydroxy-carboxylic temperature and is carried to completion at moderately acid of the Formula II with the chloroformic acid ester of elevated temperatures. In the event that X in Formula the Formula III is carried out at room temperature or 70 Vb is a halogen, the reaction must be performed in the while cooling in the presence of an acid-binding agent, presence of an acid-binding agent, such as triethylamine that is, an agent capable of tying up or neutralizing the or pyridine, and preferably in the presence of an inert 3,355,453 3. 4. organic solvent, such as benzene. Thereafter, water is in the presence of an inert organic solvent and ad added to the reaction mixture, the organic phase is de vantageously at room temperature or while cooling the canted and the organic solvent is distilled off from the reaction mixture. Suitable agents to tie up the hydrogen separated organic phase. The distillation residue is then chloride formed by the reaction are tertiary amines, advantageously heated for ten to thirty minutes at a 5 Such as triethylamine or pyridine, or also inorganic bases temperature above 100 C. in order to complete the ring such as alkali metal hydroxides, alkali metal carbonates closure. Thereafter, the final product is recrystallized in and the like; in the event that tertiary organic bases are the usual manner. used, they may also serve as the solvent medium for the Method C.-By reaction of an o-hydroxy-benzanilide reaction mixture. The ring closure reaction to which the aromatic o-O- of the formula 0. phenyl-carbamoyl-carboxylic acid XI is subjected to form a compound of the Formula I is effected either by heating compound XI to temperatures between 100 and R 200 C., advantageously in a high boiling point solvent such as Tetralin or Decalin, or by heating compound XI OH (VII) with agents which split off water, such as thionyl chlo wherein R, R2, R3 and R4 have the meanings previously ride or phosphorus halides, preferably at temperatures defined in connection with Formula I, with either phos between 80 and 100° C. This last mentioned reaction is, gene or with a chloroformic acid ester of the Formula if desired, performed in the presence of an inert solvent III above or with a carbonic acid ester of the formula and in the presence of a stoichiometric excess of the CO(ORs) (VIII) agent which promotes the splitting off of water. The separation of the reaction product from the re wherein Rs has the meanings previously defined in con action mixtures of the four above described reactions is nection with Formula II. effected in the usual manner. After distilling off the high The reaction is advantageously performed in the pres boiling point solvent or the excess of the agent which ence of an acid-binding agent and preferably in the pres promotes the splitting off of water in vacuo, the residual ence of an inert organic solvent, such as benzene, toluene, substance is purified by recrystallization. tetrahydrofuran and the like. The reaction is further ad The aromatic o-hydroxy-carboxylic acids of the For vantageously performed at elevated temperatures, pref mulas II and IV as well as the amines of the Formula erably at the boiling point of the inert organic solvent 30 VI used as starting materials in these methods are well if one is used. Suitable acid-binding agents for this reac known substances; the phenyl isocyanates of the Formula tion are tertiary organic bases, such as triethylamine, DX and the phenyl carbamic acid chlorides of the For tributylamine, pyridine or N-methyl-piperidine; an ex mula X may, if they are not already known substances, cess of the particular tertiary organic base may also be be prepared in known fashion from the amines of the employed as the solvent medium. In the reaction with the 35 Formula VI. carbonic acid ester of the formula VIII the tertiary or The following examples illustrate the preparation of a ganic base serves as a catalyst. representative number of compounds embraced by For Method D.-By reacting an aromatic o-hydroxy-car mula I above. It should be understood, however, that boxylic acid of the Formula II above with a phenyl iso the present invention is not limited to the particular ex cyanate of the formula 40 amples given below. EXAMPLE I Preparation of 3-(3',5'-dichlorophenyl)-6-chloro-benzo 1,3-oxazine-dione-(2,4) by Method A (IX) 86 gm. of 5-chloro-salicylic acid and 140 cc. of tri or a carbamic acid chloride of the formula ethylamine were dissolved at 0° C.
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