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)
Abstract
Description
Vynález se týká způsobu přípravy 2-isokyanatobenzonitrilu vzorce I.The invention relates to a process for the preparation of 2-isocyanatobenzonitrile of the formula I.
r^VCNr ^ VCN
I (I) 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).To date, the compound of formula I has been prepared by reacting isatin-3-oxime with phosphorus pentachloride in anhydrous diethyl ether at room temperature, and isolated from the reaction mixture by vacuum distillation in 78% yield (Borsche W., Sander W., Chem. Ber. 47, 2815). (1914)), or in 50% yield (Breukink KW, Verkade PE, Rec. Trav. Chim. 79, 450 (1960)), or by reaction of isatin-3-oxime with phosphorus pentachloride-phosphorus oxychloride - reaction yield not shown (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 IIThe present invention provides a novel process for the preparation of 2-isocyanatobenzonitrile of formula I. It has been found that a compound of formula I can also be prepared by reacting an isatin-3-oxime of formula 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.N-OH with thionyl chloride in excess in the absence of solvent at 55-65 ° C, the compound of formula I is purified by crystallization from cyclohexane after evaporation of unreacted thionyl chloride.
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).2-Isocyanatobenzonitrile of the formula I is used for the synthesis of 3-substituted 1- (2-cyanophenyl) ureas which have pesticidal effects or are used for the synthesis of substituted quinazolines with application in pharmacology (antimalarials, sedatives, antipyretics, antifolics) and in agriculture (pesticides) growth promoters).
PříkladExample
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.30 g (0.19 mol) of isatin-3-oxime were suspended in 100 cm @ 3 of thionyl chloride (164 g, 1.38 mol). The suspension was heated to 55-65 ° C and allowed to react for 60 minutes.
Potom byl nezreagovaný thionylchlorid vakuově oddestilován a olejovitý zbytek překrystalován z cyklohexanu.The unreacted thionyl chloride was then distilled off in vacuo and the oily residue was recrystallized from cyclohexane.
Bylo získáno 23 g (94,5 %) 2-isokyanatobenzonitrilu, teplota tání 60 až 61 °C. Bílé krystaly.23 g (94.5%) of 2-isocyanatobenzonitrile were obtained, m.p. 60-61 ° C. White crystals.
' IČ spektrum (KBr tableta)(CN) 2 230,V _ (NCO) 2 290,V c (NCO) 1 455,V (C=C) z-ť* η aS 5IR spectrum (KBr tablet) (CN) 2 230, V (NCO) 2 290, V c (NCO) 1 455, V (C = C) 2-α 5
600, 1 580, Y (CH) 3 040, 3 080 cm .600, 1580, Y (CH) 3040, 3080 cm.
Claims (1)
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 (en) |
-
1988
- 1988-11-24 CS CS773688A patent/CS273404B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS773688A1 (en) | 1990-07-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1273574B1 (en) | Process for the preparation of 4,6-dichloropyrimidine | |
| US3845055A (en) | 2,4-diaminopyrimidine-5-carboxylic acid amides | |
| US3818032A (en) | Substituted 1-phenyl-2,5-dioxo imidazolidines | |
| US3564608A (en) | Selected n-acylsubstituted-n'-hydroxyguanidines | |
| EP0052333B1 (en) | 4-fluoro-5-oxypyrazole derivate and preparation thereof | |
| CS273404B1 (en) | Method of 2-isocyanato-benzonitrile preparation | |
| US3766182A (en) | S-triazine derivatives | |
| JPH08311074A (en) | Method for producing triphenylborane amine complex compound | |
| US4226990A (en) | Triazine-diones | |
| US3910783A (en) | Dinitro-1,3-p | |
| EP0183174B1 (en) | Substituted phenoxy urea, processes for its preparation and herbicide containing it as active ingredient | |
| US3822261A (en) | 5,6-dihalo-2-fluoroalkyl-1h-imidazo(4,5-b)pyrazines | |
| Coe et al. | Reactions of polyfluoropyridines with bidentate nucleophiles: attempts to prepare deazapurine analogues | |
| US3838128A (en) | Process for the preparation of certain n-3-substituted-6-(trichloromethyl)uracils | |
| US4029785A (en) | Amino containing isonicotinic acid derivatives | |
| JPS6056962A (en) | Substituted imidazolinylbenzoic acid, ester and salt and use as herbicide | |
| CS273403B1 (en) | Method of n-methyl-n-(2-cyanophenyl)carbamoyl chloride preparation | |
| US3830822A (en) | Bis-pyridyl amines | |
| US3824281A (en) | 1-carboxamidothio-3-aryl ureas | |
| SU999974A3 (en) | Process for producing condensed derivatives of pyrimidine or their salts | |
| US4374271A (en) | Nitrophenylhydrazine compounds | |
| US4202839A (en) | Nitrophenylhydrazine compounds | |
| US4287343A (en) | Preparation of N-cyanoimidate herbicide intermediates | |
| US3468896A (en) | Method of preparing 2-pyridinealdoxime methochloride | |
| US4321202A (en) | 1-Methyl-2(alkylimino)pyrrolidines and 1-methyl 2(cycloalkylimino) pyrrolidines |