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CN (I) (2) II NH In the presence of aniline hydrochloride, 1,3-diphenylguanidine hydrochloride is an additional product; its formation can be accounted for in four ways, but proceeds in fact exclusively according to equation (2) (669). p. 201--205 ~ (27% relative to phenylbiguanide) was formulated (669) as either 2,4-diphenylmelamine or 1,2diphenylisomelamine. The melting points (216--218 ~ and 254 ~ respectively) of these two melamines subsequently synthesised (375--377) clearly suggest that the by-product was 2,4-diphenylmelamine.

In the presence of sodium ethoxide, the intermediate is not formed, and the reaction affords 2-amino-4-anilino-s-triazine-6-carboxylic acid in one stage (642). 430 The Chemisfryof Biguanides The corresponding reaction of cyclohexylbiguanide has given comparable results (607). The primary intermediate was not identified but, as a basis for discussion, was formulated as the six-membered bridged carbonyl compound (CXXlI). NPh NII (CXXl) PhNH"C"//m---n=x,n ..... HN o ~ H O (CXVlrr) BY~_N COOH (cxx) CO I COOK (CXlX) N'HC6H.

Kurzer and E. D. Pitchfork Table 2. 05 I~ef. (177) (sag) {569) (37) (37) (544) (559) (569) (569) (56P) (569) (666) (666) (301) (569) (569) (194) (30 I) (801) (lg4) (/94) (194) (194) (194) (301) (301) (19d) (194) ( 777) (569) (569) (37) (37) (194) (569) (558) (558) (558) (9) a Although n o t specified in the papers, the values are h s t e d here as first acid dissociation constants, in view of their numerical values. b A p K value was not obtained for this compound because of its strong tendency to form mice/les, even in dilute solutions.

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