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    • 164. 发明授权
    • Process for the manufacture of coumarin dyes
    • 欧马林染色体制造工艺
    • US4146712A
    • 1979-03-27
    • US770493
    • 1977-02-22
    • Peter Loew
    • Peter Loew
    • C09B57/02C07D277/62
    • C09B57/02
    • A process for the manufacture of coumarin dyes of the formula ##STR1## wherein Y represents a sulphur or an oxygen atom and the ring B can carry non-ionogenic substituents or substituted or unsubstituted fused rings, and A represents a hydrogen atom, a hydroxyl, alkoxy or phenoxy group, a nitrogen-containing heterocyclic ring system which is fused to two carbon atoms or represents a group --NR.sub.1 R.sub.2, in which R.sub.1 represents a substituted or unsubstituted alkyl or phenyl group, R.sub.2 represents a hydrogen atom or has one of the meanings assigned to R.sub.1, or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached represent a 5- or 6-membered ring system, which process comprises condensing heterocyclic products of the formula ##STR2## wherein R represents a --CN--, --COOR' or ##STR3## group, in which R' represents a substituted or unsubstituted alkyl or aryl group and each of R" and R'" independently can be the same as R' or a hydrogen atom, or together with the nitrogen atom to which they are attached form a heterocyclic 5- or 6-membered ring, and Y and B are as defined above, with the proviso that, if Y represents a sulphur atom, the reaction mixture consisting of malodinitrile and o-aminothiophenols is used as starting material, in the presence of an organic solvent and a catalytic amount of a strong acid, with an aldehyde of the formula ##STR4## wherein A is as defined above.
    • 169. 发明授权
    • Method relating to manufacture of coumarin derivatives
    • 香豆素衍生物制造方法
    • US3933847A
    • 1976-01-20
    • US426346
    • 1973-12-19
    • Masaaki OhkawaKoichi Ishii
    • Masaaki OhkawaKoichi Ishii
    • C09B57/02D06P1/16C07D405/04
    • C09B57/02
    • A coumarin dye of the formula (Ia), ##SPC1##Wherein R.sub.1 is hydrogen, chlorine or C.sub.1 -C.sub.2 alkyl, R.sub.2 and R.sub.3 are hydrogen or C.sub.1 -C.sub.4 alkyl, or a quarternary salt thereof having the formula (Ib), ##SPC2##Wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above, R.sub.4 is C.sub.1 -C.sub.2 alkyl or benzyl, and X.sup.- is an anion, is prepared by an improved method, which comprises reacting a diamine of the formula, ##SPC3##Wherein R.sub.1 is as defined above, with a compound of the formula,X -- CH.sub.2 -- Ywherein X and Y are the same or different and are carboxyl, carbamoyl, alkoxycarbonyl or cyano, in 10 to 70 % sulfuric acid to prepare an imidazolyl acetic acid of the formula, ##SPC4##Wherein R.sub.1 is as defined above, and then reacting the imidazolyl acetic acid with a compound of the formula, ##SPC5##Wherein R.sub.2 and R.sub.3 are as defined above, to obtain the dye (Ia), or further reacting the resulting dye (Ia) with an alkylating agent to obtain the dye (Ib).
    • 式(Ia)的香豆素染料,WHEREIN R1是氢,氯或C1-C2烷基,R2和R3是氢或C1-C4烷基,或其具有式(Ib)的季盐,WHEREIN R1,R2和 R3如上定义,R4是C1-C2烷基或苄基,X'是阴离子,是通过一种改进的方法制备的,其包括使下式的二胺,其中R 1如上定义,与化合物 其中X和Y相同或不同,为10-70%硫酸中的羧基,氨基甲酰基,烷氧基羰基或氰基,以制备下式的咪唑基乙酸,其中R 1如上定义 然后使咪唑基乙酸与下式化合物(其中R 2和R 3如上定义)反应,得到染料(Ia),或进一步使得到的染料(Ia)与烷基化剂反应得到染料 (Ib)。