CS270981B1 - 2-isothiocyanatobenzonitrile and method of its production - Google Patents
2-isothiocyanatobenzonitrile and method of its production Download PDFInfo
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- CS270981B1 CS270981B1 CS88695A CS69588A CS270981B1 CS 270981 B1 CS270981 B1 CS 270981B1 CS 88695 A CS88695 A CS 88695A CS 69588 A CS69588 A CS 69588A CS 270981 B1 CS270981 B1 CS 270981B1
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- isothiocyanatobenzonitrile
- water
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- production
- thiophosgene
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Abstract
Description
a způsobu jeho výroby reakcí anthraniloni trilu s thiofosgenem v inertním organickém rozpouštědle, s výhodou dichlormethanu v přítomnosti vody.and a process for its preparation by reacting anthranilone tril with thiophosgene in an inert organic solvent, preferably dichloromethane in the presence of water.
Látka I a způsob její výroby nebyly doposud v literatuře popsány. 3e známo, že příbuzné arylisothiokyanáty lze připravit reakcí arylaminu s thiofosgenem ve vodné suspenzi, resp. emulzi, případně v chloroformovém roztoku v přítomnosti vody (Dyson G. M., George H. 3.,Substance I and the process for its preparation have not been described in the literature. It is known that related arylisothiocyanates can be prepared by reacting arylamine with thiophosgene in an aqueous suspension, respectively. emulsion, optionally in a chloroform solution in the presence of water (Dyson G. M., George H. 3.,
3. Chem. Soc. 1924, 1702; Oyson G. M., George H. 3., Hunter R. F., 3. Chem. Soc. 1927, 1189; Oyson G. M. Chem. Ind. 30 (1954), 934; Tietze E., Pe- Tersen S,, Oomagk G., Chem. Ber. 86 (1953 ), 314 ).3. Chem. Soc. 1924, 1702; Oyson G. M., George H. 3., Hunter R. F., 3. Chem. Soc. 1927, 1189; Oyson G.M. Chem. Indian. 30 (1954) 934; Tietze E., P.Tersen S, Oomagk G., Chem. Ber. 86 (1953) 314).
Nyní bylo nalezeno, že také látku I lze připravit reakcí anthranilonitrolu s thiofosgenem v inertním organickém rozpouštědle, s výhodou dichlormethanu v přítomnosti vody.It has now been found that compound I can also be prepared by reacting anthranilonitrile with thiophosgene in an inert organic solvent, preferably dichloromethane in the presence of water.
PříkladExample
Ke směsi obsahující roztok 28,7 g (0,25 mol) thioíosgenu v 30 cm^ dichlormethanu a 70 cm^ vody byl během 10 minut přikapán roztok obsahující v 50 cn? dichlormethanu 23,6 g (0,20 mol) anthranilonitrilu, Směs byla intenzívně míchána po dobu 120 až 180 minut za laboratorní teploty. Potom byla organická vrstva oddělena, vysušena a rozpouštědlo oddestilováno.To a mixture containing a solution of 28.7 g (0.25 mol) of thiosulfene in 30 cm @ 3 of dichloromethane and 70 cm @ 3 of water was added dropwise a solution containing at 50 cm @ 3 of water over 10 minutes. of dichloromethane 23.6 g (0.20 mol) of anthranilonitrile. The mixture was stirred vigorously for 120 to 180 minutes at room temperature. Then, the organic layer was separated, dried and the solvent distilled off.
Rekrystalizací odparku z petroletheru bylo získáno 28,3 g (88,4 %) 2-isothiokyanatobenzonitrilu.Recrystallization of the residue from petroleum ether gave 28.3 g (88.4%) of 2-isothiocyanatobenzonitrile.
Bílé jehlice, t. tání 60 až 61° C.White needles, m.p. 60-61 ° C.
Rf (Silufol UV 254, eluováno CHCl-j) 0,833.R f (Silufol UV 254, eluted with CHCl j) 0.833.
IR spektrum (roztok v CHBr-j) : (NCS) 2 070, V* (CN) 2 240, Y (C = C) 1 595, 1 585, 1 495,IR spectrum (CHBr-j solution): (NCS) 2 070, V * (CN) 2 240, Y (C = C) 1595, 1585, 1495,
1450 cm’1.1450 cm -1 .
2-Isothiokyanatobenzonitri 1 se používá pro syntézu 3-substituovaných 1-(2-kyanfeny1) thiomočovin, které se používají jako reagenty pro syntézu kondenzovaných pyгimidinových heterocyklů, využívaných ve farmakologii a v zemědělství.2-Isothiocyanatobenzonitrile is used for the synthesis of 3-substituted 1- (2-cyanophenyl) thioureas, which are used as reagents for the synthesis of fused pyrimidine heterocycles used in pharmacology and agriculture.
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS88695A CS270981B1 (en) | 1988-02-04 | 1988-02-04 | 2-isothiocyanatobenzonitrile and method of its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS88695A CS270981B1 (en) | 1988-02-04 | 1988-02-04 | 2-isothiocyanatobenzonitrile and method of its production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS69588A1 CS69588A1 (en) | 1990-01-12 |
| CS270981B1 true CS270981B1 (en) | 1990-08-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS88695A CS270981B1 (en) | 1988-02-04 | 1988-02-04 | 2-isothiocyanatobenzonitrile and method of its production |
Country Status (1)
| Country | Link |
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| CS (1) | CS270981B1 (en) |
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1988
- 1988-02-04 CS CS88695A patent/CS270981B1/en unknown
Also Published As
| Publication number | Publication date |
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| CS69588A1 (en) | 1990-01-12 |
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