CS266827B1 - 2-lothothiocyanato-3-cyano-4,5,6,7-tetrahydrobenzo [b] thiophene and process for its preparation - Google Patents
2-lothothiocyanato-3-cyano-4,5,6,7-tetrahydrobenzo [b] thiophene and process for its preparation Download PDFInfo
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- CS266827B1 CS266827B1 CS877826A CS782687A CS266827B1 CS 266827 B1 CS266827 B1 CS 266827B1 CS 877826 A CS877826 A CS 877826A CS 782687 A CS782687 A CS 782687A CS 266827 B1 CS266827 B1 CS 266827B1
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Abstract
Řešení se týká 2-isothiokyanato-3- -kyan-4,5,6,7-tetrahydrobenzo [b] thiofenu vzorce I a způsobu jeho výroby reakcí 2- -amino-3-kyan-4,5,6,7-tetrahydrobenzo[b] - thiofenu vzorce II s thiofosgenem v inertním organickém rozpouštědle v přítomnosti uhličitanu vápenatého nebo hydrogenuhličitanu sodného či draselného při teplotě 20 až 25 °C. Látka vzorce I slouží jako meziprodukt pro syntézu produktů s herbicidními účinky a látek využitelných ve farmakologii a v zemědělství.The solution relates to 2-isothiocyanato-3- -cyano-4,5,6,7-tetrahydrobenzo [b] thiophene of formula I and a method for its production by reacting 2- -amino-3-cyano-4,5,6,7-tetrahydrobenzo [b] - thiophene of formula II with thiophosgene in an inert organic solvent in the presence of calcium carbonate or sodium or potassium bicarbonate at a temperature of 20 to 25 ° C. The substance of formula I serves as an intermediate for the synthesis of products with herbicidal effects and substances useful in pharmacology and agriculture.
Description
Vynález se týká 2-isothiokyanato-3-kyan-4,5,6,7-tetrahydrobenzo [b]thiofenu vzorce I (I) a způsobu jeho výroby. Látka vzorce I a způsob její výroby nebyly doposud ρ ' cy, avšak je známo, že příbuzné arylisothiokyanáty lze připravit reakcí arylaminu s thiofosgenem v přítomnosti vody. Výtěžky reakce se pohybují od 60 do 97 % (Dyson G. M., George H. J. , J. Chem. Soc. 125, 1 702 (1924), Dyson G. M., Chem. Ind. 30, 934 (1954), Tietze E., Petersen S., Domagk G. , Ber. 86, 314 (1953).
Předmětem vynálezu je nová látka, 2-isothiokyanato-3-kyan-4,5,6,7-tetrahydrobenzoJbJ-thiofen vzorce I. Bylo nalezeno, že látku vzorce I lze připravit reakcí 2-amino-3-kyan-4,5,6,7--tetrahydro [bj thiofenu vzorce II (II) s thiofosgenem v inertním rozpouštědle v přítomnosti uhličitanu vápenatého nebo hydrogen-uhličitanu sodného či draselného při teplotě 20 až 25 °C. 2-isothiokyanato-3-kyan-4,5,6,7-tetrahydrobenzo [b]thiofen se používá pro syntézy Ν'-substituovaných N-/2-(3-kyan-4,5,6,7-tetrahydrobenzo [bj thíenyl)/thíomočovin, které mají herbicidní účinky nebo se využívají jako prekursory pro syntézu kondenzovaných pyrimidi-nových heterocyklú využívaných ve farmakologii (sedativa, antitusika, antimalarika, antifolika) a zemědělství (herbicidy, stimulátory růstu) . Přiklad K suspenzi obsahující 50 cm"* dichlormethanu, 28,7 g (0,25 mol) thiofosgenu a 34 g (0,40 mol) jemně rozetřeného hydrogenuhličitanu sodného byla za intenzivního míchání za teploty místnosti po dobu 20 minut přikapávána suspenze obsahující 36,7 g (0,20 mol) 2-amino--3-kyan-4,5,6 ,'7-tetrahydro [b] thiofenu v 800 cm* dichlormethanu. Po 60 minutách reakce od počátku přidávání aminové složky byla reakce ukončena, rozpouštědlo a nereagovaný thio-fosgen byly odpařeny na rotační vakuové odparce. Produkt byl překrystalován ze směsi benzen--cyklohexan.
Bylo získáno 38,2 g (86,7 %) 2-isothiokyanato-3-kyan-4,5,6,7-tetrahydrobenzo[b]thiofenu. Žlutá krystalická látka, teplota tání 68 až 70 °C. IČ spektrum (suspenze v bromoformu) : λ) (CN) 2 225, \) (N=C=S) 2 000, Ό (C=C) 1 565 , "S5 (CH) 2 850, 2 870, 2 950 cm-1.
The present invention relates to 2-isothiocyanato-3-cyano-4,5,6,7-tetrahydrobenzo [b] thiophene of formula I (I) and to a process for its preparation. The compound of formula (I) and the process for its preparation have not been previously known, but related arylisothiocyanates are known to be prepared by reacting arylamine with thiophosgene in the presence of water. Reaction yields range from 60 to 97% (Dyson GM, George HJ, J. Chem. Soc. 125, 1702 (1924), Dyson GM, Chem. Ind. 30, 934 (1954), Tietze E., Petersen S , Domagk G., Ber., 86, 314 (1953).
The present invention provides a novel compound, 2-isothiocyanato-3-cyano-4,5,6,7-tetrahydrobenzo [b] thiophene of formula I. It has been found that the compound of formula I can be prepared by the reaction of 2-amino-3-cyano-4,5, 6,7-tetrahydro [b] thiophene of formula II (II) with thiophosgene in an inert solvent in the presence of calcium carbonate or sodium or potassium bicarbonate at 20-25 ° C. 2-isothiocyanato-3-cyano-4,5,6,7-tetrahydrobenzo [b] thiophene is used for the synthesis of Ν'-substituted N- [2- (3-cyano-4,5,6,7-tetrahydrobenzo [b] thienyl) thioureas which have herbicidal activity or are used as precursors for the synthesis of condensed pyrimidine heterocycles used in pharmacology (sedatives, antitussives, antimalarials, antifolics) and agriculture (herbicides, growth promoters). Example K A suspension containing 36% of sodium bicarbonate, 28.7 g (0.25 mol) of thiophosgene and 34 g (0.40 mol) of finely divided sodium bicarbonate was added dropwise to the suspension at 50 DEG C. for 20 minutes. 7 g (0.20 mol) of 2-amino-3-cyano-4,5,6,7-tetrahydro- [b] thiophene in 800 cm < -1 > of dichloromethane. the solvent and the unreacted thio-phosgene were evaporated on a rotary evaporator, and the product was recrystallized from benzene-cyclohexane.
38.2 g (86.7%) of 2-isothiocyanato-3-cyano-4,5,6,7-tetrahydrobenzo [b] thiophene were obtained. Yellow crystalline, mp 68-70 ° C. IR spectrum (suspension in bromoform): λ) (CN) 2 225, (N = C = S) 2 000, Ό (C = C) 1 565, "S5 (CH) 2 850, 2 870, 2 950 cm-1.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS877826A CS266827B1 (en) | 1987-11-02 | 1987-11-02 | 2-lothothiocyanato-3-cyano-4,5,6,7-tetrahydrobenzo [b] thiophene and process for its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS877826A CS266827B1 (en) | 1987-11-02 | 1987-11-02 | 2-lothothiocyanato-3-cyano-4,5,6,7-tetrahydrobenzo [b] thiophene and process for its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS782687A1 CS782687A1 (en) | 1989-05-12 |
| CS266827B1 true CS266827B1 (en) | 1990-01-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS877826A CS266827B1 (en) | 1987-11-02 | 1987-11-02 | 2-lothothiocyanato-3-cyano-4,5,6,7-tetrahydrobenzo [b] thiophene and process for its preparation |
Country Status (1)
| Country | Link |
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| CS (1) | CS266827B1 (en) |
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1987
- 1987-11-02 CS CS877826A patent/CS266827B1/en unknown
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| CS782687A1 (en) | 1989-05-12 |
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