CS273403B1 - Method of n-methyl-n-(2-cyanophenyl)carbamoyl chloride preparation - Google Patents
Method of n-methyl-n-(2-cyanophenyl)carbamoyl chloride preparation Download PDFInfo
- Publication number
- CS273403B1 CS273403B1 CS773588A CS773588A CS273403B1 CS 273403 B1 CS273403 B1 CS 273403B1 CS 773588 A CS773588 A CS 773588A CS 773588 A CS773588 A CS 773588A CS 273403 B1 CS273403 B1 CS 273403B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- methyl
- cyanophenyl
- carbamoyl chloride
- thionyl chloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 title description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 16
- XVDVCPOWCPQHNC-UHFFFAOYSA-N 3-hydroxyimino-1-methylindol-2-one Chemical compound C1=CC=C2N(C)C(=O)C(=NO)C2=C1 XVDVCPOWCPQHNC-UHFFFAOYSA-N 0.000 claims abstract description 5
- QLTNCVKOAUFRSL-UHFFFAOYSA-N N-(2-cyanophenyl)-N-methylcarbamoyl chloride Chemical compound CN(C(=O)Cl)C1=C(C=CC=C1)C#N QLTNCVKOAUFRSL-UHFFFAOYSA-N 0.000 claims abstract description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000004821 distillation Methods 0.000 claims abstract description 3
- 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
- 239000000575 pesticide Substances 0.000 abstract description 3
- -1 3-substituted 1-methyl-1-(2-cyanphenyl)urea Chemical class 0.000 abstract description 2
- 239000003430 antimalarial agent Substances 0.000 abstract description 2
- 238000006243 chemical reaction Methods 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
- 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
- 235000013877 carbamide Nutrition 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
- 239000000543 intermediate Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 230000000144 pharmacologic 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
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Vynález se týká způsobu přípravy N-methyl-M-(2-kyanfenyl)karbamoylchloridu vzorce I.The invention relates to a process for the preparation of N-methyl-N- (2-cyanophenyl) carbamoyl chloride of the formula I.
(I)(AND)
Látka vzorce I byla doposud připravována reakcí l-methylisatín-3-oximu s chloridem fosforečným v bezvodém diethyletheru za laboratorní teploty, z reakční směsi byla izolována destilací za sníženého tlaku - výtěžek reakce není uveden (Borsche W., Sander W., Chem. Ber. 47, 2815 /1914/).To date, the compound of formula I has been prepared by reacting 1-methylisatin-3-oxime with phosphorus pentachloride in anhydrous diethyl ether at room temperature, isolated from the reaction mixture by distillation under reduced pressure - yield of reaction not shown (Borsche W., Sander W., Chem. Ber. 47, 2815 (1914).
Předmětem vynálezu je nový způsob přípravy N-methyl-N-(2-kyanfenyl)karbamoylchloridu vzorce I. Bylo nalezeno, že látku vzorce I lze také připravit reakcí l-methylisatin-3-oximu vzorce II Π—rN_0H The present invention provides a novel process for the preparation of N-methyl-N- (2-cyanophenyl) carbamoyl chloride of formula I. It has been found that the compound of formula I can also be prepared by reacting 1-methylisatin-3-oxime of formula II Π —r N_0H
CHo s thionylchloridem v nadbytku bez přítomnosti rozpouštědla pří teplotě 40 až 50 °C, látka vzorce I je po odpaření nezreagovaného thionylchloridu přečištěna krystalizaci z cyklohexanu.CH 2 with thionyl chloride in excess in the absence of solvent at 40 to 50 ° C, the compound of formula I is purified by crystallization from cyclohexane after evaporation of unreacted thionyl chloride.
N-Methyl-N-(2-kyanfenyl)karbamoylchlorid je používán pro syntézu 3-substituovaných l-methyl-l-(2-kyanfenyl)močovin, které mají pesticidní účinky nebo se využívají jako meziprodukty k syntéze substituovaných chinazolinů s aplikací ve farmakologii (antimalarika, sedativa, antifolika) a v zemědělství (pesticidy, růstové stimulátory).N-Methyl-N- (2-cyanophenyl) carbamoyl chloride is used for the synthesis of 3-substituted 1-methyl-1- (2-cyanophenyl) ureas which have pesticidal effects or are used as intermediates in the synthesis of substituted quinazolines with pharmacological application ( antimalarials, sedatives, antifolics) and in agriculture (pesticides, growth promoters).
PříkladExample
V 50 cm3 thionylchloridu (82 g, 0,7 mol) bylo suspendováno 17,6 g (0,1 mol) 1-methylisatin-3-oximu. Suspenze byla zahřáta na teplotu 40 až 50 °C a ponechána reagovat 45 minut.17.6 g (0.1 mol) of 1-methylisatin-3-oxime was suspended in 50 cm 3 of thionyl chloride (82 g, 0.7 mol). The suspension was warmed to 40-50 ° C and allowed to react for 45 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 připraveno 18 g (92,8 %) N-methyl-N-C2-kyanfenyl)k'arbamoylchloridu, teplota tání 59 až 60 °C. Bílá krystalická látka. IČ spektrum (KBr tableta): V(C=N) 2 210,18 g (92.8%) of N-methyl-N-C2-cyanophenyl) carbamoyl chloride were prepared, m.p. 59-60 ° C. White crystalline solid. IR (KBr tablet): V (C = N) 2 210,
V (C=0) 1 740 , 7(C=C) 1 590, 1 450, ý (CH) 3 050, 2 990, 2,880,^(0-(0 1 295 cm1.Λ (C = O) 1740, 7 (C = C) 1590, 1450, γ (CH) 3050, 2990, 2.880, δ (0- (0 1295 cm -1 )) .
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS773588A CS273403B1 (en) | 1988-11-24 | 1988-11-24 | Method of n-methyl-n-(2-cyanophenyl)carbamoyl chloride preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS773588A CS273403B1 (en) | 1988-11-24 | 1988-11-24 | Method of n-methyl-n-(2-cyanophenyl)carbamoyl chloride preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS773588A1 CS773588A1 (en) | 1990-07-12 |
| CS273403B1 true CS273403B1 (en) | 1991-03-12 |
Family
ID=5426988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS773588A CS273403B1 (en) | 1988-11-24 | 1988-11-24 | Method of n-methyl-n-(2-cyanophenyl)carbamoyl chloride preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS273403B1 (en) |
-
1988
- 1988-11-24 CS CS773588A patent/CS273403B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS773588A1 (en) | 1990-07-12 |
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