(12) Translation of european patent specification

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1 (12) Translation of european patent specification (11) NO/EP B1 (19) NO NORWAY (1) Int Cl. C07D 417/14 (06.01) Norwegian Industrial Property Office (21) Translation Published (80) Date of The European Patent Office Publication of the Granted Patent (86) European Application Nr (86) European Filing Date (87) The European Application s Publication Date (30) Priority.07.16, IT, MI1316 (84) Designated Contracting States: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR (73) Proprietor ENI S.p.A., Piazzale E. Mattei 1, Rome, IT-Italia (72) Inventor SANTARELLI, Samuele, Via Costantino Porta, I-280 NOVARA, IT-Italia RICCI, Marco, Via Fra Dolcino 19, I-280 Novara, IT-Italia FUSCO, Roberto, Passaggio Privato Roggia Mora 19, I-280 Novara, IT-Italia (74) Agent or Attorney Murgitroyd & Company, Scotland Street, GB-G8PL GLASGOW, Storbritannia (4) Title PROCESS FOR THE SYNTHESIS OF BENZOTHIADIAZOLE COMPOUNDS (6) References Cited: MEIJER E W ET AL: "Band-Gap Engineering of Donor-Acceptor-Substituted PI-conjugated polymers", CHEMISTRY - A EUROPEAN JOURNAL, WILEY - V C H VERLAG GMBH & CO. KGAA, WEINHEIM, DE, vol. 4, no. 7, 1 January 1998 ( ), pages , XP , ISSN: , DOI: DOI:.02/(SICI)21-376(199807)4:7<1 23::AID-CHEM123>3.3.CO;2-W

2 Enclosed is a translation of the patent claims in Norwegian. Please note that as per the Norwegian Patents Acts, section 66i the patent will receive protection in Norway only as far as there is agreement between the translation and the language of the application/patent granted at the EPO. In matters concerning the validity of the patent, language of the application/patent granted at the EPO will be used as the basis for the decision. The patent documents published by the EPO are available through Espacenet ( or via the search engine on our website here: NO/EP293449

3 1 PATENTKRAV 1. Fremgangsmåte for fremstilling av forbindelser som har generell formel (A) 2 30 (A) de to tienylgrupper -C 4 HS(R 1 ) 2 er de samme, hver R 1 i tienylgruppen er uavhengig valgt blant H, lineært eller forgrenet alkyl, sykloalkyl, aryl, alkylaryl, alkoksyl, substituert alkoksyl, hver R 2 er uavhengig valgt blant H, lineært eller forgrenet alkyl, sykloalkyl, aryl, alkylaryl, alkoksyl, substituert alkoksyl eller de naboliggende R 1 -grupper i tienylgruppen og/eller de naboliggende R 2 -grupper, er bundet til hverandre og danner, sammen med karbonatomene de er bundet til, en syklus eller et polysyklisk system, alifatisk eller aromatisk, muligens inneholdende ett eller flere heteroatomer, hvor nevnte fremgangsmåte omfatter å bringe, i nærvær av en Pd-holdig katalysator, ved en temperatur høyere enn 1 C og i nærvær av et løsemiddel som er valgt blant dimetylsulfoksid (DMSO) og dimetylformamid (DMF), en forbindelse som har formelen (B), X er et halogen valgt blant Cl, Br og I, hver R 2 er uavhengig valgt blant H, lineært eller forgrenet alkyl, sykloalkyl, aryl, alkylaryl, alkoksyl, substituert alkoksyl, eller de naboliggende R 2 -grupper er bundet til hverandre og danner, sammen med karbonatomene de er bundet til, en syklus eller et polysyklisk system, alifatisk eller aromatisk, muligens inneholdende ett eller flere heteroatomer, (B) til å reagere med en forbindelse som har formelen (C)

4 2 (C) hver R 1 er uavhengig H, lineært eller forgrenet alkyl, sykloalkyl, aryl, alkylaryl, alkoksyl, substituert alkoksyl, eller de naboliggende R 1 -grupper er bundet til hverandre og danner, sammen med karbonatomene de er bundet til, en syklus eller et polysyklisk system, alifatisk eller aromatisk, muligens inneholdende ett eller flere heteroatomer, og R 3 er et alkyl som inneholder fra 1 til 6 karbonatomer. 2. Fremgangsmåte ifølge krav 1, hvor, når i det minste én av R 1 -gruppene og/eller i det minste én av R 2 -gruppene er lineært eller forgrenet alkyl, sykloalkyl, aryl, alkylaryl, alkoksyl, substituert alkoksyl, nevnte gruppe inneholder fra 1 til karbonatomer Fremgangsmåte ifølge krav 1, hvor alle R 1 - og R 2 -grupper er H. 4. Fremgangsmåte ifølge krav 1, hvor de naboliggende R 1 -grupper av tienylgruppen og/eller de naboliggende R 2 -grupper, sammen med karbonatomene de er bundet til, danner en syklus eller et polysyklisk system, alifatisk eller aromatisk, muligens inneholdende ett eller flere heteroatomer, inneholdende fra 3 til 14 karbonatomer.. Fremgangsmåte ifølge krav 1, hvor R 3 er et alkyl som inneholder fra 1 til 4 karbonatomer Fremgangsmåte ifølge krav 1 for fremstilling av forbindelsen som har formelen (A), hvor alle R 1 - og R 2 -grupper er H, hvilken fremgangsmåte omfatter å bringe forbindelsen som har formelen (B), hvor X er et halogen valgt blant Cl, Br og I, og R 2 -gruppene er H, til å reagere med forbindelsen som har formelen (C), hvor R 1 -gruppene er H, og R 3 er alkyl inneholdende fra 1 til 6 karbonatomer Fremgangsmåte ifølge krav 1 eller 6 for fremstilling av forbindelsen som har formelen (A), hvor alle R 1 - og R 2 -grupper er H, hvilken fremgangsmåte omfatter å bringe forbindelsen som har formelen (B), hvor X er Br og R 2 -gruppene er H, til å reagere med forbindelsen som har formelen (C), hvor R 1 -gruppene er hydrogen, og R 3 er n-butyl.

5 3 8. Fremgangsmåte ifølge krav 1, hvor molforholdet mellom forbindelsen som har formelen (C) og forbindelsen som har formelen (B), er lik Fremgangsmåte ifølge krav 1, hvor palladiumet har et oksidasjonstall på (0) eller (II).. Fremgangsmåte ifølge krav 9, hvor palladiumet er i form av et kompleks. 11. Fremgangsmåte ifølge krav, hvor palladiumkomplekset velges blant: - bis(trifenylfosfin)palladium(ii)-klorid [Pd(PPh 3 ) 2 Cl 2 ], - bis(trifenylfosfin)palladium(ii)-acetat [Pd(PPh 3 ) 2 (OAc) 2 ], - tetrakis(trifenylfosfin)palladium(0) [Pd(PPh 3 ) 4 ], - bis(dibenzylidenaceton)palladium(0) [Pd(dba) 2 ; dba: C 6 H CH=CHCOCH=CHC 6 H ], - bis(acetonitril)palladium(ii)-klorid, [Pd(Ch 3 CN) 2 Cl 2 ], - benzyl[bis(trifenylfosfin)]palladium(ii)-klorid [C 6 H CH 2 Pd(PPh 3 ) 2 Cl]. 12. Fremgangsmåte ifølge krav 1, hvor palladiumet anvendes i en mengde i området fra 0,01 til 0,1 mol per 0 mol av forbindelse som har formelen (B). 13. Fremgangsmåte ifølge krav 12, hvor palladiumet er i en mengde i området fra 0,04 til 0,06 mol per 0 mol av forbindelse som har formelen (B) Fremgangsmåte ifølge krav, hvor palladiumkomplekset tildannes i det samme reaksjonsmiljø.. Fremgangsmåte ifølge krav 1, hvor reaksjonen utføres ved en temperatur som er høyere enn 1 C, fortrinnsvis er temperaturen høyere enn 1 C og lavere enn eller lik med 160 C, mer foretrukket er temperaturen i området fra 140 til 0 C. MURG *

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