Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1999-01-24
2000-09-19
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C07D25168
Patent
active
061214442
DESCRIPTION:
BRIEF SUMMARY
The invention relates to an improved process for the preparation of compounds of the formula ##STR1## in which n is 0 or 1, two alkyl radicals which are optionally interrupted by a heteroatom from the series O, N and S, together with the N-atom to which they are bonded may form a saturated 5- or 6-membered heterocycle.
The compounds (I) are important optical brighteners, inter alia for polyamide, cellulose, paper and detergent.
Preferred alkali metal ions are sodium and potassium ions, and a preferred ammonium ion is the triethanolammonium ion.
The alkyl radicals in the combined terms N-alkylamino and N,N-dialkylamino are preferably taken to mean alkyl radicals having up to 4 carbon atoms, which may be interrupted by an O atom and/or may carry a substituent customary in the chemistry of whiteners, such as hydroxyl, cyano, carbamoyl or sulfo.
Examples of saturated 5- and 6-membered heterocycles which can be formed from the two alkyl radicals of the N,N-dialkylamino group and the nitrogen atom to which they are bonded are, for example, pyrrolidine, piperidine, N-methylpiperazine, N-2-hydroxyethylpiperazine and, in particular, morpholine.
Processes for the preparation of compounds (I) from cyanuric chloride, a 4,4'-diaminostilbene-2,2'-disulfonic acid salt of the formula ##STR2## an aniline of the formula ##STR3## in which M and n are as defined above, and an amine XH (VI), X being in each case defined as in (I), are described; DE-AS (German Published Specification) 1 250 830, GB Patent Specification 1 114 021 and 1 174 631, U.S. Pat. No. 3,532,692, PL Patent Specification 76 705, RO Patent Specification 62 947, DD Patent Specification 154 778 and 159 334, CS Patent Specification 228 871 and JP Patent Specification 62/106 965.
Surprisingly, it has now been found that unexpected advantages result when the reaction of the reaction product of cyanuric chloride and (II) with (IV) is carried out in the presence of the amine (VI) as acid-absorber.
The invention thus provides a process for the preparation of compounds of the formula (I) by reaction of cyanuric chloride with a 4,4'-diaminostilbene-2,2'-disulfonic acid salt of the formula (II) in the molar ratio 2:1, subsequent reaction of the resulting compound of the formula ##STR4## in which M is as defined above, with 2 equivalents of an aniline of the formula ##STR5## in which M and n are as defined above, and subsequent reaction of the resulting compound of the formula ##STR6## in which M and n are as defined above, with 2 equivalents of an amine of the general formula XH (VI), amine (VI) as acid-absorber and that, for this purpose, amine (VI) is metered in at a rate such that the pH is maintained in the range from 3.0 to 7.0, preferably in the range from 3.5 to 6.0, in particular in the range from 4.0 to 6.0, and that for the reaction of (V), the amine (VI) is freed from its protonated form by a suitable base.
The process according to the invention leads to a clear increase in the reaction rate, which can be exploited to give a reaction at considerably lower temperatures (i.e. under relatively mild conditions) than previously without conversion losses.
The process according to the invention generally involves, in a first stage, adding a 4,4'-diaminostilbene-2,2'-disulfonic acid dialkali metal salt of the formula (II) in the form of an aqueous solution to an aqueous cyanuric chloride-suspension in the temperature range from 0 to 25.degree. C. and in the pH range from 3.5 to 5.5 in the presence of or with the simultaneous addition of a water-soluble, acid-binding agent for neutralization of the hydrochloric acid liberated. Water-soluble acid-binding agents suitable for this purpose are, for example, alkali metal hydroxides, alkali metal carbonates and alkali metal hydrogencarbonates, such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate and potassium hydrogencarbonate, or triethanolamine. These can be used in solid or liquid form, e.g. gradually via a conveying screw, or advantageously also in the form of t
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Brockmann Rolf
Eckstein Udo
Feldhues Ulrich
Vogt Uwe
Balasubramanian Venkataraman
Bayer Aktiengesellschaft
Gil Joseph C.
Henderson Richard E. L.
Shah Mukund J.
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