Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfonic acids or salts thereof
Patent
1998-01-09
1999-10-05
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Sulfonic acids or salts thereof
562 44, 562 45, 562 73, 558411, 564305, 568 27, 568 28, 568 29, 546347, C07C30504
Patent
active
059627301
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel sulfonyl compounds of the formula I ##STR2## where n is 0, 1 or 2, hydroxyl or an alkali-detachable group, oxygen atoms in ether-function, C.sub.1 C.sub.6 -alkyl with or without amino or C.sub.1 -C.sub.4 -alkanoylamino substitutions C.sub.1 -C.sub.6 -alkoxy, hydroxyl, halogen, nitro, amino, C.sub.1 -C.sub.4 -alkanoylamino, mono- or di(C.sub.1 -C.sub.6 -alkyl)amino, hydroxysulfonyl, carboxyl carbamoyl, mono- or di(C.sub.1 -C.sub.6 -alkyl)carbamoyl, sulfamoyl, mono- or di(C.sub.1 -C.sub.6 -alkyl)sulfamoyl, cyano or a radical of the formula (NH--).sub.m (CH.sub.2 --).sub.q SO.sub.2 --Y, where m is 0 or 1, q is 0, 2 or 3, and Y is as defined above.
It is an object of the present invention to provide novel aromatic sulfonyl compounds having an additional thioether, sulfoxide or sulfonyl group in the molecule. The novel compounds shall be easy to obtain and advantageously useful as intermediates for dyes.
We have found that this object is achieved by the above-defined aromatic sulfonyl compounds of the formula I.
Any alkyl or alkylene appearing in the formulae recited herein may be straight-chain or branched R.sup.1, R.sup.2 and R.sup.3 are each, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, aminomethyl, 2-aminoethyl, 2- or 3-aminopropyl, 2- or 4-aminobutyl, 5-aminopentyl, 6-aminohexyl, formylaminomethyl, 2-formylaminoethyl, 2- or 3-formylaminopropyl, 2- or 4-formylaminobutyl, 5-formylaminopentyl, 6-formylaminohexyl, acetylaminomethyl, 2-acetylaminoethyl, 2- or 3-acetylaminopropyl, 2- or 4-acetylaminobutyl, 5-acetylaminopentyl, 6-acetylaminohexyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy, fluorine, chlorine, bromine, mono- or dimethylamino, mono- or diethylamino, mono- or dipropylamino, mono- or diisopropylamino, mono- or dibutylamino, mono- or dipentylamino, mono- or dihexylamino, mono- or dimethylcarbamoyl, mono- or diethylcarbamoyl, mono- or dipropylcarbamoyl, mono- or dibutylcarbamoyl, mono- or dipentylcarbamoyl, mono- or dihexylcarbamoyl, mono- or dimethylsulfamoyl, mono- or diethylsulfamoyl, mono- or dipropylsulfamoyl, mono- or dibutylsulfamoyl, mono- or dipentylsulfamoyl, mono- or dihexylsulfamoyl, formylamino, acetylamino, propionylamino, butyrylamino or isobutyrylamino.
E is for example (CH.sub.2).sub.3, (CH.sub.2).sub.4, (CH.sub.2).sub.5, (CH.sub.2).sub.6, CH(CH.sub.3)CH.sub.2, CH(CH.sub.3)CH(CH.sub.3), (CH.sub.2).sub.2 O(CH.sub.2).sub.2, (CH.sub.2).sub.2 O(CH.sub.2).sub.3, (CH.sub.2).sub.3 O(CH.sub.2).sub.3 or (CH.sub.2).sub.2 O(CH.sub.2).sub.2 O(CH.sub.2).sub.2.
Q is hydroxyl or an alkali-detachable group. Examples of such groups include chlorine, bromine, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl, OSO.sub.3 H, SSO.sub.3 H, OP(O)(OH).sub.2, C.sub.1 -C.sub.4 -alkylsulfonyloxy, phenylsulfonyloxy, C.sub.1 -C.sub.4 -alkanoyloxy, di(C.sub.1 -C.sub.4 -alkyl)amino or a radical of the formula ##STR3## where L.sup.1, L.sup.2 and L.sup.3 are independently of each other C.sub.1 -C.sub.4 -alkyl or benzyl and An.sup..crclbar. is in each case one equivalent of an anion. Examples of suitable anions include fluoride, chloride, bromide, iodide, mono- di- or trichloroacetate, methanesulfonate, benzenesulfonate and 2- or 4-methylbenzenesulfonate.
Preference is given to sulfonyl compounds of the formula I where n is 0 or 2, in particular 2.
Preference is further given to sulfonyl compounds of the formula I where E is C.sub.3 - or C.sub.4 -alkylene, in particular C.sub.3 -alkylene.
Preference is further given to sulfonyl compounds of the formula I where Ar is the radical of benzene
Preference is further given to sulfonyl compounds of the formula I where R.sup.1 is C.sub.1 -C.sub.4 -alkyl with or without amino or C.sub.1 -C.sub.4 -alkanoylamino substitution, nitro, amino or C.sub.1 -C.sub.4 -alkanoylamino and R.sup.2 and R.sup.3 are independently of each other hydrogen, C.sub.1 -C.s
REFERENCES:
patent: 2098759 (1937-11-01), Reppe
Beilstein ref no 3137596 preparation found in J chem Soc 2433,2440, Ford-Moore, 1949.
Marschner Claus
Patsch Manfred
BASF - Aktiengesellschaft
Geist Gary
Volleim Jean F.
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