Production of 3-substituted- and 1,3-disubstituted-2,4(1h,3h)-quinazolinediones, andthe 2,4 thio and dithio analogues thereof

摘要

1,137,111. Process for preparation of substituted quinazolinediones. MAUMEE CHEMICAL CO. 15 June, 1966 [15 June, 1965], No. 26683/66. Heading C2C. Compounds of the Formula II wherein X is a halogen, nitro, trifluoromethyl or alkyl group of 1 to 22 carbon atoms, n is an integer from 0 to 4, so that X can be the substituent at any of the 4 positions of the benzene ring, Y is oxygen or sulphur, RSP11/SP can be hydrogen or a lower n-alkyl group having 1 to 6 carbon atoms, and, when RSP11/SP is hydrogen, RSP1/SP can be an alkyl group having 1 to 22 carbon atoms, a cycloalkyl group of 3 to 22 carbon atoms, an alkaryl or aralkyl group of 7 to 22 carbon atoms, an alkenyl or alkynyl group of 3 to 22 carbon atoms, a naphthyl or phenyl group, a nitro-, halo or trifluoromethyl-substituted naphthyl, phenyl, alkylnaphthyl or alkylphenyl group or a carboxyphenyl or a carbethoxy amino group or a 5 or 6 membered heterocycle, or when RSP11/SP is a lower n-alkyl group, RSP1/SP can be a lower nalkyl group of 1 to 6 carbon atoms, isopropyl, sec-butyl, a cycloalkyl group of 3 to 6 carbon atoms, or a phenyl group, are prepared by reacting together phosgene or thiophosgene with an o-amino- or o-substituted amino-N-substitutedbenzamide or -thiobenzamide, in a suitable solvent, e.g. p-dioxane, and heating the resulting reaction mixture to evolve HCl. The o-substituted amino-N-substituted benzamides are produced by alkylating isatoic anhydride or a substituted isatoic anhydride with sodium hydride and an organic halide, and then aminating the product. The thiobenzamide starting materials are prepared by reacting the corresponding benzamide with phosphorus pentasulphide. Reference has been directed by the Comptroller to Specification 1,059,271.