EP 1021412 A1 20000726 - NITRATION OF AROMATIC COMPOUNDS
Title (en)
NITRATION OF AROMATIC COMPOUNDS
Title (de)
NITRIERUNG VON AROMATISCHE VERBINDUNGEN
Title (fr)
NITRATATION DE COMPOSES AROMATIQUES
Publication
Application
Priority
- GB 9603020 W 19961209
- GB 9525789 A 19951216
Abstract (en)
[origin: CA2240644A1] A method of nitrating electron-deficient carbocyclic or heterocyclic aromatic compounds such as pyridines, diazines and triazines and benzenoid aromatics having electron-withdrawing substituents involves first reacting the aromatic species with a sulphilimine species or with the corresponding N-alkali metal salt thereof to generate an N-(hetero)aryl-S,S-dialkyl, diaryl or alkylarylsulphilimine derivative. This intermediate may then be readily oxidised under relatively mild conditions using a peroxycarboxylic acid such as m-chloroperbenzoic acid, peracetic or peroxytrifluoroacetic acid. Good yields of nitrated products are obtained including some previously unprepared. The novel N-alkali(alkylaryl)sulphilimine reagents are prepared by reacting an alkali metal hydride, an alkali metal hydrogenous base or an alkyl lithium with the corresponding sulphilimine. Preferred salts are the N-lithio types and the preferred sulphilimine is diphenylsulphilimine. Where the salt is used reaction should be in an aprotic solvent but if the sulphilimine per se is the reagent a polar solvent is used.
IPC 1-7
C07D 213/76; C07D 213/61; C07D 241/16; C07D 241/20; C07D 239/42; C07D 239/30; C07D 251/42; C07D 251/26; C07C 381/10; C07C 205/12; C07B 43/02
IPC 8 full level
C07C 201/10 (2006.01); C07C 205/12 (2006.01); C07C 381/10 (2006.01); C07D 213/61 (2006.01); C07D 213/76 (2006.01); C07D 239/42 (2006.01); C07D 241/16 (2006.01); C07D 241/20 (2006.01); C07D 251/44 (2006.01); C07D 251/46 (2006.01)
CPC (source: EP)
C07C 201/10 (2013.01); C07C 201/16 (2013.01); C07C 381/10 (2013.01); C07D 213/61 (2013.01); C07D 213/76 (2013.01); C07D 239/42 (2013.01); C07D 241/16 (2013.01); C07D 241/20 (2013.01); C07D 251/44 (2013.01); C07D 251/46 (2013.01)
Citation (search report)
See references of WO 9722590A1
Designated contracting state (EPC)
CH DE FR GB IE IT LI NL SE
DOCDB simple family (publication)
GB 2308119 A 19970618; GB 9525789 D0 19960214; CA 2240644 A1 19970626; CZ 186798 A3 19981014; CZ 291529 B6 20030312; EP 1021412 A1 20000726; GB 2322857 A 19980909; GB 2322857 B 20000329; GB 9811567 D0 19980729; IL 124960 A0 19990126; IL 124960 A 20030212; NO 309524 B1 20010212; NO 982753 D0 19980615; NO 982753 L 19980817; WO 9722590 A1 19970626; ZA 9610559 B 19970624
DOCDB simple family (application)
GB 9525789 A 19951216; CA 2240644 A 19961209; CZ 186798 A 19961209; EP 96941744 A 19961209; GB 9603020 W 19961209; GB 9811567 A 19961209; IL 12496096 A 19961209; NO 982753 A 19980615; ZA 9610559 A 19961213