CS273404B1 - Method of 2-isocyanato-benzonitrile preparation - Google Patents
Method of 2-isocyanato-benzonitrile preparation Download PDFInfo
- Publication number
- CS273404B1 CS273404B1 CS773688A CS773688A CS273404B1 CS 273404 B1 CS273404 B1 CS 273404B1 CS 773688 A CS773688 A CS 773688A CS 773688 A CS773688 A CS 773688A CS 273404 B1 CS273404 B1 CS 273404B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- thionyl chloride
- synthesis
- oxime
- isatin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 5
- FQLNVWAFXQUXGW-UHFFFAOYSA-N 2-isocyanatobenzonitrile Chemical compound O=C=NC1=CC=CC=C1C#N FQLNVWAFXQUXGW-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 16
- XXIJFHJUUXTXIX-UHFFFAOYSA-N 3-nitroso-1H-indol-2-ol Chemical compound Oc1[nH]c2ccccc2c1N=O XXIJFHJUUXTXIX-UHFFFAOYSA-N 0.000 claims abstract description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 239000000575 pesticide Substances 0.000 abstract description 3
- -1 3-substituted 1-(2-cyanphenyl)urea Chemical class 0.000 abstract description 2
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 2
- 239000003430 antimalarial agent Substances 0.000 abstract description 2
- 239000002221 antipyretic Substances 0.000 abstract description 2
- 239000000932 sedative agent Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 2
- 230000000078 anti-malarial effect Effects 0.000 abstract 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 239000003324 growth hormone secretagogue Substances 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000907661 Pieris rapae Species 0.000 description 1
- 229940033495 antimalarials Drugs 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- PQUHFRSGVHFXNT-UHFFFAOYSA-N pcl5 pocl3 Chemical compound ClP(Cl)(Cl)=O.ClP(Cl)(Cl)(Cl)Cl PQUHFRSGVHFXNT-UHFFFAOYSA-N 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Vynález se týká způsobu přípravy 2-isokyanatobenzonitrilu vzorce I.
r^VCN
I (I)
Látka vzorce I byla doposud připravována reakcí isatin-3-oximu s chloridem fosforečným v bezvodém diethyletheru za laboratorní teploty, z reakčni směsi byla izolována destilací za vakua ve výtěžku 78 % (Borsche W., Sander W., Chem. Ber. 47, 2815 /1914/), respektive v 50 % výtěžku (Breukink K.W., Verkade P.E., Rec. trav. Chim. 79, 450 /1960/), popřípadě reakcí isatin-3-oximu se směsí chlorid fosforečný-fosforoxychlorid - výtěžek reakce neuveden (Schoeter G., Seidler Ch., J. prakt. Chem. 105, 336).
Předmětem vynálezu je nový způsob přípravy 2-isokyanatobenzonitrilu vzorce I. Bylo nalezeno, že látku vzorce I lze také připravit reakcí isatin-3-oximu vzorce II
-^N-OH s thionylchloridem v nadbytku bez přítomnosti rozpouštědla při teplotě 55 až 65 °C, látka vzorce I je po odpaření nezreagovaného thionylchloridu přečištěna krystalizací z cyklohéxanu.
2-Isokyanatobenzonitril vzorce I se používá pru syntézy 3-substituovaných l-(2-kyanfenyl)močovin, které mají pesticidní účinky nebo se využívají k syntéze substituovaných chinazolinů s aplikací ve farmakologii (antimalarika, sedativa, antipyretika, antifolika) a v zemědělství (pesticidy, stimulátory růstu).
Příklad
Ve 100 cm thionylchloridu (164 g, 1,38 mol) bylo suspendováno 30 g (0,19 mol) isatin-3-oximu. Suspenze byla zahřáta na teplotu 55 až 65 °C a ponechána reagovat 60 minut.
Potom byl nezreagovaný thionylchlorid vakuově oddestilován a olejovitý zbytek překrystalován z cyklohexanu.
Bylo získáno 23 g (94,5 %) 2-isokyanatobenzonitrilu, teplota tání 60 až 61 °C. Bílé krystaly.
' IČ spektrum (KBr tableta)(CN) 2 230,V _ (NCO) 2 290,V c (NCO) 1 455,V (C=C) z-ť* η aS 5
600, 1 580, Y (CH) 3 040, 3 080 cm .
Claims (1)
- PŘEDMĚT VYNÁLEZUZpůsob přípravy 2-isokyanatobenzonitrilu vzorce I vyznačující se tím, že se ponechá reagovat isatin-3-oxim vzorce II •^>1-jsN-OH (II) s thionylchloridem v nadbytku bez přítomnosti rozpouštědla při teplotě 55 až 65 °C a látka vzorce I je po oddestilováni nezreagovaného thionylchloridu překrystalována z cyklohexanu.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS773688A CS273404B1 (en) | 1988-11-24 | 1988-11-24 | Method of 2-isocyanato-benzonitrile preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS773688A CS273404B1 (en) | 1988-11-24 | 1988-11-24 | Method of 2-isocyanato-benzonitrile preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS773688A1 CS773688A1 (en) | 1990-07-12 |
| CS273404B1 true CS273404B1 (en) | 1991-03-12 |
Family
ID=5427000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS773688A CS273404B1 (en) | 1988-11-24 | 1988-11-24 | Method of 2-isocyanato-benzonitrile preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS273404B1 (cs) |
-
1988
- 1988-11-24 CS CS773688A patent/CS273404B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS773688A1 (en) | 1990-07-12 |
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