Production of cyanomethyl heterocycles

    公开(公告)号:GB975165A

    公开(公告)日:1964-11-11

    申请号:GB2668063

    申请日:1963-07-05

    Applicant: BASF AG

    Abstract: Compounds of the formula in which A is a benzene or naphthalene radical substituted by the two nitrogen atoms in the ortho- or peri-position, and which may be substituted by nonionic radicals (such as halogen, alkyl and alkoxy), and R1 is hydrogen or substituted or unsubstituted alkyl or aryl, are obtained by reaction of with NC.CH2COOR2, where R2 is the radical of a primary or secondary alcohol, at 160 DEG -220 DEG C. in the presence of an aromatic sulphonic acid. Inert solvents may be used. Specified sulphonic acids are p-toluene-, benzene- and 2-naphthalene-sulphonic acids. Examples prepare 2-cyanomethylbenzimidazole and its 5 (or 6)-methyl; 1-phenyl; 1-methyl; 5 (or 6)-chloro; 1-methyl-5 (or 6)-methyl; 5 (or 6)-methoxy; 1-b -cyanoethyl; and 1-b -hydroxyethyl derivatives; and 2-cyano-methyl perimidine. 1,2- and 2,3-diaminonaphthalene are also specified as starting materials.

    Monoazo dyes of the benzene-azo-naphthalene series

    公开(公告)号:GB950156A

    公开(公告)日:1964-02-19

    申请号:GB2220662

    申请日:1962-06-08

    Applicant: BASF AG

    Abstract: 1-Amino -4- (b -hydroxyethoxy)-benzene sulphuric acid monoester is prepared by treating 1-amino -4- (b -hydroxyethoxy)-benzene hydrochloride with sulphuric acid. The g -toluylsulphonate of 1-amino -4- b , g -dihydroxypropoxy - benzene hydrochloride is prepared by adding p-toluenesulphonic acid with cooling to a paste of 4-formylamino-phenylglycide ether in acetone, reacting for 15 hours at room temperature and adding hydrochloric acid to precipitate the hydrochloride.ALSO:The invention comprises monoazo dyes of formula wherein R1 is a hydroxyl or a substituted or unsubstituted phenyl group, R is an ethylene or propylene radical which may be substituted by a hydroxyl group, A is a phenylene group which may be substituted other than by water-solubilizing groups (i.e. groups which readily impart solubility in water, excluding weakly hydrophilic groups such as methyl sulphone) and m is 0 or 1. The dyes are prepared by the azo coupling procedure using sulphuric acid or benzene sulphonic acid esters of hydroxy-ethoxy- or -propoxy-phenylamines as diazo compounds and 21,31-hydroxynaphthoyl-2-methoxy- or 2,5-dimethoxy-1-aminobenzene as coupling components. Alternatively, suitable hydroxy-ethoxy- or -propoxy-substituted azo dyes are esterified with sulphuric acid or benzene sulphonic acids, or substances yielding such acids in the reaction, e.g. chlorosulphonic acid and benzene sulphonic acid halides. The preferred dyes are those having the esterified hydroxyalkoxy group ortho to the azo bridge. The dyes give red shades on wool, polyesters, polyamides and polyurethanes. The preparation of the dyes is described in examples.

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