PL147987B2 - Procedure for receiving new 2,2'-/arenodiylo/bis pirolo 3,4-b 1,4 benzothiazine-1,3/2h-9h/diones - Google Patents

Procedure for receiving new 2,2'-/arenodiylo/bis pirolo 3,4-b 1,4 benzothiazine-1,3/2h-9h/diones Download PDF

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PL147987B2
PL147987B2 PL26195286A PL26195286A PL147987B2 PL 147987 B2 PL147987 B2 PL 147987B2 PL 26195286 A PL26195286 A PL 26195286A PL 26195286 A PL26195286 A PL 26195286A PL 147987 B2 PL147987 B2 PL 147987B2
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bis
benzothiazine
diones
arenodiylo
pirolo
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PL26195286A
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Polish (pl)
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PL261952A2 (en
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Description

Przedmiotem wynalazku jest sposób otrzymywania nowych 2,2'-/arenodiylo/bis-{pirolo [3,4-b][l,4]-benzotiazyno-l,3 /2H,9H/-dionów} o ogólnym wzorze 1, w którym X oznacza grupe 1,4-fenylenowa lub karbonyloiminodi-l,4-fenylenowa. Nowe zwiazki otrzymywane sposobem wedlug wynalazku stanowia pigmenty organiczne do przyrzadzania farb i lakierów.Sposobem wedlug wynalazku na zwiazek o ogólnym wzorze 2, w którym X ma wyzej podane znaczenie, dziala sie 2-aminotiofenolanem cynku. Reakcje prowadzi sie w kwasie octowym w temperaturze wrzenia.Wynalazek ilustruja nastepujace przyklady, w których procenty oznaczaja procenty wagowe, a stopnie temperatury podano w stopniach Celsjusza.Przyklad I. Mieszanine 8,47 g (0,02 mola) l,r-/l,4-fenylo/bis[3-chloro-4-dimetyloamino- lH-pirolo-2,5-dionu], 6,90 g (0,022 mola) 2-aminotiofenolanu cynku oraz 1 dcm3 kwasu octowego ogrzewano do wrzenia 2 godziny. Po ochlodzeniu odsaczono osad, przemyto 150 cm3 9% kwasu solnego, trzykrotnie porcjami po 150 cm3 wody, trzykrotnie porcjami po 150 cm3 etanolu i wysu¬ szono. Surowy produkt (9,92 g) ekstrahowano w aparacie Soxhleta za pomoca 400 cm3 acetonu do uzyskania bezbarwnego roztworu. Otrzymano 9,72 g (wydajnosc 95%) zielonego pigmentu o temperaturze topnienia 300°, odznaczajacego sie dobrymi trwalosciami na rozpuszczalniki organiczne.IR (KBr): 3330 (i/NH), 1760, 1710 (vc=o), 1660 (vc=c), 1510 cm"1 (vCAr -.. CAr).Przyklad II. Mieszanine 10,84 g (0,02 mola) l,lVkarbonyloiminodi-4,l-fenyleno/bis[3- chloro-4-dimetyloamino-lH-pirolo-2,5-dionu], 6,90 g (0,022 mola) 2-aminotiofenolanu cynku oraz 1 dcm3 kwasu octowego ogrzewano do wrzenia 2 godziny. Po ochlodzeniu odsaczono osad, przemyto 150 cm3 9% kwasu solnego, trzykrotnie porcjami po 150 cm3 wody, trzykrotnie porcjami po 150 cm3 etanolu i wysuszono. Surowy produkt (12,00 g) ekstrahowano w aparacie Soxhleta 400 cm3 acetonu do uzyskania lekkozóltego roztworu. Otrzymano 11,36 g (wydajnosc 90%) zólto¬ zielonego pigmentu o temperaturze topnienia 300°, charakteryzujacego sie dobrymi trwalosciami na rozpuszczalniki organiczne.IR (KBr): 3320 (vNH), 1770, 1760, 1710, 1700 (i/c=o), 1660 (i/c=c), 1600 (<5nh), 1510 cm"1 (vCAr • * »CAr).2 147 987 Zastrzezenie patentowe Sposób otrzymywania nowych 2,2'-/arenodiylo/bis-{pirolo[3,4-b][ 1,4]-benzotiazyno-1,3 /2H,9H/-dionów} o ogólnym wzorze 1, w którym X oznacza grupe 1,4-fenylenowa lub karbonyloiminodi-4,1-fenylenowa, znamienny tym, ze na zwiazek o ogólnym wzorze 2, w którym X ma wyzej podane znaczenie, dziala sie 2-aminotiofenolanem cynku w kwasie octowym w tempera¬ turze wrzenia. ii ° ° H wzfflU H3? 0 0 CH3 o o mm 2 Pracownia Poligraficzna UP RP.Naklad 100 egz.Cena 1500 zl PLThe subject of the invention is a process for the preparation of new 2,2 '- (arenediyl) bis- {pyrrolo [3,4-b] [1,4] benzothiazine-1,3 (2H, 9H) -diones} with the general formula 1, wherein X is 1,4-phenylene or carbonyldi-1,4-phenylene. The new compounds according to the invention are organic pigments for the preparation of paints and varnishes. According to the invention, the compound of the general formula II, in which X has the meaning given above, is treated with zinc 2-aminothiophenate. The reactions are carried out in acetic acid at boiling point. The invention is illustrated by the following examples, in which the percentages are percentages by weight and the temperature degrees are in degrees Celsius. Example I. Mixture 8.47 g (0.02 mol) l, r- / l , 4-phenyl) bis [3-chloro-4-dimethylamino-1H-pyrrole-2,5-dione], 6.90 g (0.022 mol) of zinc 2-aminothiophenate and 1 dm 3 of acetic acid was heated to reflux for 2 hours. After cooling, the precipitate is filtered off, washed with 150 cm.sup.3 of 9% hydrochloric acid, three times with 150 cm.sup.3 of water, three times with 150 cm.sup.3 of ethanol and dried. The crude product (9.92 g) was extracted in a Soxhlet apparatus with 400 ml of acetone until a colorless solution was obtained. 9.72 g (95% yield) of a green pigment with a melting point of 300 °, showing good stability to organic solvents, IR (KBr): 3330 (i / NH), 1760, 1710 (vc = o), 1660 (vc) = c), 1510 cm -1 (vCAr - .. CAr). Example II. A mixture of 10.84 g (0.02 mol) 1,1Vcarbonylimiminodi-4,1-phenylene / bis [3-chloro-4-dimethylamino- 1H-pyrrole-2,5-dione], 6.90 g (0.022 mol) of zinc 2-aminothiophenolate and 1 dm3 of acetic acid were heated to reflux for 2 hours After cooling, the precipitate was filtered off, washed with 150 cm3 of 9% hydrochloric acid, three times with portions of 150 cm3 of water, three times with 150 cm3 of ethanol and dried The crude product (12.00 g) was extracted in a Soxhlet apparatus with 400 cm3 of acetone until a light yellow solution was obtained. 11.36 g (90% yield) of a yellow-green pigment, m.p. 300 °, characterized by good stability to organic solvents IR (KBr): 3320 (vNH), 1770, 1760, 1710, 1700 (i / c = o), 1660 (i / c = c), 1600 (<5nh) , 1510 cm "1 (vCAr • * »CAr) .2 147 987 Patent claim Method of obtaining new 2,2 '- (arenediyl) bis- {pyrrolo [3,4-b] [1,4] -benzothiazine-1,3 (2H, 9H) -diones} of general formula I in which X is 1,4-phenylene or carbonyliminodi-4,1-phenylene, characterized in that the compound of general formula II in which X is as defined above is treated with zinc 2-aminothiophenate in acetic acid at boiling point. ii ° ° H wfflU H3? 0 0 CH3 o o mm 2 Printing House of the Polish Patent Office, 100 copies. Price: PLN 1,500 PL

Claims (1)

1. Zastrzezenie patentowe Sposób otrzymywania nowych 2,2'-/arenodiylo/bis-{pirolo[3,4-b][ 1,4]-benzotiazyno-1,3 /2H,9H/-dionów} o ogólnym wzorze 1, w którym X oznacza grupe 1,4-fenylenowa lub karbonyloiminodi-4,1-fenylenowa, znamienny tym, ze na zwiazek o ogólnym wzorze 2, w którym X ma wyzej podane znaczenie, dziala sie 2-aminotiofenolanem cynku w kwasie octowym w tempera¬ turze wrzenia. ii ° ° H wzfflU H3? 0 0 CH3 o o mm 2 Pracownia Poligraficzna UP RP.Naklad 100 egz. Cena 1500 zl PL1. Claim The method of obtaining new 2,2 '- (arenediyl) bis- {pyrrolo [3,4-b] [1,4] -benzothiazine-1,3 (2H, 9H) -diones} with the general formula 1, wherein X is 1,4-phenylene or carbonyliminodi-4,1-phenylene, characterized in that the compound of formula II, wherein X is as defined above, is treated with zinc 2-aminothiophenate in acetic acid at a temperature round of boiling. ii ° ° H wfflU H3? 0 0 CH3 o o mm 2 Printing House of the Polish Patent Office of the Republic of Poland. Mintage 100 copies. Price PLN 1500 PL
PL26195286A 1986-10-17 1986-10-17 Procedure for receiving new 2,2'-/arenodiylo/bis pirolo 3,4-b 1,4 benzothiazine-1,3/2h-9h/diones PL147987B2 (en)

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PL26195286A PL147987B2 (en) 1986-10-17 1986-10-17 Procedure for receiving new 2,2'-/arenodiylo/bis pirolo 3,4-b 1,4 benzothiazine-1,3/2h-9h/diones

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PL26195286A PL147987B2 (en) 1986-10-17 1986-10-17 Procedure for receiving new 2,2'-/arenodiylo/bis pirolo 3,4-b 1,4 benzothiazine-1,3/2h-9h/diones

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PL147987B2 true PL147987B2 (en) 1989-08-31

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008515943A (en) * 2004-10-13 2008-05-15 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング Heterocyclic substituted bisarylurea derivatives as kinase inhibitors

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008515943A (en) * 2004-10-13 2008-05-15 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング Heterocyclic substituted bisarylurea derivatives as kinase inhibitors

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