HU204776B - Process for producing n-acylaminals - Google Patents

Process for producing n-acylaminals Download PDF

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Publication number
HU204776B
HU204776B HU902500A HU250088A HU204776B HU 204776 B HU204776 B HU 204776B HU 902500 A HU902500 A HU 902500A HU 250088 A HU250088 A HU 250088A HU 204776 B HU204776 B HU 204776B
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Hungary
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formula
cyano
mol
isocyanates
known manner
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HU902500A
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English (en)
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HU902500D0 (en
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Winfried Lunkenheimer
Dieter Berg
Wilhelm Brandes
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Bayer Ag
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Publication of HU902500D0 publication Critical patent/HU902500D0/hu
Publication of HU204776B publication Critical patent/HU204776B/hu

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    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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Description

A találmány tárgya eljárás az új és a 200 749 lajstromhatású Ν,Ν’-diaciI-amináIok. (H) általános képletű iníermedíeqeinek előállítására.
A (Π) általános képletben 5
R1 jelentése 1-4 szénatomos alkilcsoport,
R2 jelentése hidrogénatom,
Z jelentése NH2xHY,
HY szervetlen vagy szerves sav ekvivalense.
HY előnyösen ásványi savekvivalens, például sósav 10 vagy karbonsav, például oxálsav.
A (II) általános képleté 2-ciano-2-oximino-aceíamidok (tehát - ahol Z jelentése NH2xHY) nem ismertek.
Előállításuk azonban ismert módon úgy történhet, hogy egy (EV) általános képletű izocianátot - ahol R1 15 ésR2jelentése a fenti-ismert módon hidrolizálunk, és a keletkező amint ismert módon sóként izoláljuk. A (IV) általános képletű izocianátok hidrolízisét hígítószer jelenlétében hajtjuk-végre. Előnyösen használhasd ketonokat, például acetont ' A reakció hőmérsékletét a (TV) általános képletű izocianátok hidrolízisénél tág határokon belül változtathatjuk, általában -20 és +150 °C, előnyösen 20és 25 80 °C között dolgozunk. A találmány szerinti eljárás során a (IV) általános képletű izocianátok hidrolízisét előnyösen in srtu végezzük, vfe feleslegben. Akelezkező amin izolálását só formájában sav hozzáadásával, például sósav hozzá- 30 adásával hajtjuk végre, majd ezt követően a szokásos módon feldolgozzuk.
A (TV) általános képletű izocianátok újak, Előállíthatók ismert módon, például úgy, hogy egy (VI) általános képletű amídot - ahol R1 és R2 35 jelentése a fenti - ismert módon, adott esetben hígító- szer jelenlétében oxidálunk („Hofmann-féle” lebontás), és a keletkezett (IV) általános képletű izocianátot adott esetben izolálás nélkül közvetlenül tovább reagáltathatjuk. ' 40
Oxidálószerként előnyösen nátrium-hipokloritot vagy -bromitot, ólom-tetraacetátot, valamint 1,1bisz(frifluor-acetoxi)-jöd-benzolthasználunk(J. Chem.
Soc. Chem. Com. 1982,280. o.).
Hígítószerként inért szerves oldószereket használ- 45 tünk, például étereket, mint tetrahidrofuránt, dioxánt vagy dimetil-étereket vagy mtrileket,példáulacetonitrilt. :
Ha a (IV) általános képletű izocianátot közvetlenül továbbreagálíatjuk, akkor a hígítőszerként vizet vagy 50 alkoholokat is használhatunk, vagy ezek inért szerves oldószerekkel képezett elegyeit, ilyen például a víz és aeetonitril elegye.
A reakció hőmérséklete az oxidációnál tág határok között változhat, általában -20 és 120 °C, előnyösen 0 55 és 40 °C között dolgozunk.
A találmány szerinti eljárás során az oxidációt előnyösen az oxidálószer kevés feleslegében végezzük, nélkül közvetlenül tovább reagáltatjuk.
(55)képletűvegyület
12,4 g (0,067 mól) N-[(E)-2-ciano-2-metoiíi-iminoacetílj-glicinamid 150 ml aeetonitril és víz 1:1 térfogatarányú elegyével készített oldatát 31 g (0,07 mól) 98 t%-os, I,I-bísz-(trifIuor-acetoxi)-jód-benzollal elegyítjük, és az elegyet nitrogén átvezetésével 5 óra hosszat keverjük szobahőmérsékleten, Vákuumban bepároljuk, az olajos maradékot kétszer etil-acetáttal lepárolva szárítjuk, feloldjuk 70 ml etil-acetátban, hozzáadunk 10 ml 25t%dörzsöljük, és aeetonitril és éter elegyéböl átkristályosítjuk. 9,8 g (76%)N-amino-metil-(E)-2-cíano-2-metoxiimino-acetamid-hidrokloridotkapunk.
Op.: 122-124 °C (bomlik).
(56) képletű vegyület .
56,6 g (0,252 mól) 95 t%-os N-[(E)-2-ciano-2-meloxiirrúno-acetil]-glicin-etil-észter 300 ml izopropanollal készített Oldatába 0-10 °C hőmérsékleten telítésig ammóniát vezetünk, és az elegyet 4 napig szobahőmérsékleten állni hagyjuk Ezalatt még kétszer vezetünk be ammóniát. Lehűtjük 0 °C-ra, majd a csapadékot leszívatjuk, hideg izopropanollal mossuk, és szobahőmérsékleten szárítjuk.
g (69%) N-a-[(E)-2-ciano-2-metoxi-imino-acelilj-glicinamidot kapunk.
Op.: 170-172 °C. ' (57) képletű vegyület '
60,5 g (0,427 mól) glicin-etil-észter-hídrokloridot 450 ml diklór-metánban szuszpendálunk, hozzáadunk metil-amino-piridint, a reakcióelegyet 15 percig keverjük 20 °C hőmérsékleten, hozzácsepegtetünk 62,5 g (0,427 mól) 2-ciano-2-metiI-oximino-acetil-klorid (E-izomer) oldatot0 °Chőmérsékleten 1órán belül. Eztkövetően az elegyet! óra hosszat 0°C-on, majd 5 óra hosszat szobahőmérsékleten keverjük, és az oldatot 2 napig állni hagyjak, szobahőmérsékleten. 2x300 ml 1 mólos sósavval, majd 2x300 ml vízzel mossuk' majd nátrium-szulfát felett szárítjuk, és vákuumban bepároljuk.
81,0 g (89%) N-a-(2-ciano-2-metoxi-imino-acetil)glicin-etil-észtert (E-izomer) kapunk barna olaj formá(58) képletű vegyület g (0,12 mól) 2-ciano-2-metoxi-imino-acetát (Eizomer) káliumsóját 250: ml száraz éterben szuszpendáljük, és néhány csepp dimetil-formamid hozzáadása után 0 °C hőmérsékleten 76,2 g (0,6 mól) oxalil-klorikeveqűk 0 °C hőmérsékleten leszűrjük, és a szűrletet vákuumban szobahőmérsékleten bepároljuk.
/ 13,7 g (77%) 2-ciano-2-metoxi-imino-acetil-kloridot (E-izomer) kapunk sárga olaj formájában, amelyet azonnal továbbreagáltatunk.
(59) képletű vegyület
124,8 g (0,672 mól) 84%-os 2-cíano-2-metoxi-imino-ecetsav-etil-észter (E-izomer) 500 ml etanollal ké1
HU 204776 Β szítért oldatába 20 °C hőmérsékleten hozzácsepegtetünk 45,1 g (0,806 mól) kálium-hidroxidot 500 ml vízben Oldva, és a reakcióelegyet 1 óra hosszat keveqük 40 °C hőmérsékleten. Az oldatot vákuumban 40 °C-on bepároljuk, a maradékot metanollal 30 percig elkeverjük, leszívatjuk és etanollal, acetonitrillel és diklór-metánnal mossuk és szobahőmérsékleten szárítjuk.
58,6 g (53%) 2-ciano-2-metoxi-imino-acetát (E-izomer) káliumsóját kapjuk, (60) képletű vegyület
164 g (1 mól) 2-ciano-2-hidroximino-ecetsav-etil-észter, nátrium-klorid [G. Kinast, Liebigs Ann. Chem, 1981. 1561] és 138 g porított kálium-karbonát 1,5 liter acetonnal készített szuszpenziójába 161 g (1,25 mól) 98t%-os dimetil-szulfátot csepegtetünk 30 perc alatt, és a reakcióelegyet 3 óra hosszat melegítjük visszafolyató hűtő alatt. Lehűtés Után Kieselguron leszűq'ük és bepároljuk.
124,8 g 2-ciano-2-metoxi-imino-ecetsav-etil-észtert (E-izomer) kapunk pirosasbama olaj formájában 85%os tisztaságban gázkromatográfiás analízis szerint. A » kitermelés 68%-os. Ötszörös mennyiségű Kieselgel 60-on végzett kromatografálás után kloroformmal 93%-os világossárga olajat kapunk.

Claims (1)

  1. Eljárás (Π) általános képletű N-(2-ciano-2-oximinoacetil)-aminálok - ahol R1 jelentése 1-4 szénatomos alkilcsoport,
    R2 jelentése hidrogénatom,
    Z jelentése NH2xHY,
    HY szervetlen vagy szerves sav ekvivalense előállítására, azzal jellemezve, hogy egy (VI) általános képletű amidot- ahol R1 és R2 jelentése a fenti- ismert módon, a Hoffmann-féle lebontás körülményei között, adott esetben hígítószer jelenlétében oxidálunk, majd egy így kapott (IV) általános képletű izocianátot- ahol R1 és R2 jelentése a fenti - adott esetben izolálás nélkül ismert módon hidrolizálunk és a keletkező amint ismert módon sóként izoláljuk.
HU902500A 1987-08-25 1988-08-25 Process for producing n-acylaminals HU204776B (en)

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DE3938287A1 (de) * 1989-11-17 1991-05-23 Bayer Ag Substituierte aminale
DE4426753A1 (de) * 1994-07-28 1996-02-01 Bayer Ag Mittel zur Bekämpfung von Pflanzenschädlingen
DE19829113A1 (de) 1998-06-10 1999-12-16 Bayer Ag Mittel zur Bekämpfung von Pflanzenschädlingen
ATE278322T1 (de) * 1998-06-17 2004-10-15 Bayer Cropscience Ag Mittel zur bekämpfung von pflanzenschädlingen

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US3984568A (en) * 1975-09-11 1976-10-05 E. I. Du Pont De Nemours And Company Fungicidal cyclopropyl substituted 2-cyanoacetamide derivatives
US4178383A (en) * 1976-05-28 1979-12-11 Bayer Aktiengesellschaft Fungicidally active oxime-ethers of isonitrosocyanoacetamides
DE2626828A1 (de) * 1976-06-15 1977-12-22 Bayer Ag Neue carbamidsaeureoximester, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
US4188401A (en) * 1977-06-04 1980-02-12 Bayer Aktiengesellschaft Combating fungi with 1-(ω-substituted pentyl)-3-(2-cyano-acetyl)-ureas
DE3133359A1 (de) * 1981-08-22 1983-03-10 Bayer Ag, 5090 Leverkusen Substituierte anilinmonomethylen-oxime, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenschutzmittel
EP0201999A1 (en) * 1985-04-16 1986-11-20 Imperial Chemical Industries Plc Substituted 2-cyano-2-oximino-acetamides, processes for their production and their use as fungicides
DE3602243A1 (de) * 1985-06-13 1986-12-18 Bayer Ag, 5090 Leverkusen E-isomere von n(pfeil hoch)(alpha)(pfeil hoch)-(2-cyan-2-alkoximino-acetyl)-aminosaeurederivaten und -peptiden
DE3625460A1 (de) * 1986-07-28 1988-02-04 Bayer Ag N-(2-cyan-2-oximinoacetyl)-aminonitrile
DE3625497A1 (de) * 1986-07-28 1988-02-11 Bayer Ag E/z-isomerengemische und reine z-isomere von n(pfeil hoch)(alpha)(pfeil hoch)-(2-cyan-2-alkoximinoacetyl)-aminosaeurederivaten und -peptiden
DE3702283A1 (de) * 1987-01-27 1988-08-04 Bayer Ag Verfahren zur herstellung von 2-cyano-2-oximino-acetamid-derivaten

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DE3728277A1 (de) 1989-03-09
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HU902500D0 (en) 1990-08-28
PT88277A (pt) 1989-06-30
US4945111A (en) 1990-07-31
EP0304758B1 (de) 1991-09-04
JPH0196164A (ja) 1989-04-14
EP0304758A1 (de) 1989-03-01
HU200749B (en) 1990-08-28
PT88277B (pt) 1995-03-01
DE3864631D1 (de) 1991-10-10

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