SE448089B - Sett att framstella acylhydrazoner av formylettiksyraester - Google Patents
Sett att framstella acylhydrazoner av formylettiksyraesterInfo
- Publication number
- SE448089B SE448089B SE8007042A SE8007042A SE448089B SE 448089 B SE448089 B SE 448089B SE 8007042 A SE8007042 A SE 8007042A SE 8007042 A SE8007042 A SE 8007042A SE 448089 B SE448089 B SE 448089B
- Authority
- SE
- Sweden
- Prior art keywords
- alcohol
- hydrazons
- formyletic
- general formula
- acid ester
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- -1 acyl hydrazones Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- OAKURXIZZOAYBC-UHFFFAOYSA-N 3-oxopropanoic acid Chemical compound OC(=O)CC=O OAKURXIZZOAYBC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- AQMUJYIIJQCRQB-UHFFFAOYSA-N ethyl n-carbamoyl-3-oxopropanehydrazonate Chemical compound CCOC(CC=O)=NNC(N)=O AQMUJYIIJQCRQB-UHFFFAOYSA-N 0.000 description 1
- UZVGCOHVBOGBSI-UHFFFAOYSA-N ethyl n-ethoxycarbonyl-3-oxopropanehydrazonate Chemical compound CCOC(=O)NN=C(CC=O)OCC UZVGCOHVBOGBSI-UHFFFAOYSA-N 0.000 description 1
- FMVJYQGSRWVMQV-UHFFFAOYSA-N ethyl propiolate Chemical compound CCOC(=O)C#C FMVJYQGSRWVMQV-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229960005335 propanol Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BXCZJWHJYRELHY-UHFFFAOYSA-N thiadiazole-5-carboxylic acid Chemical class OC(=O)C1=CN=NS1 BXCZJWHJYRELHY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/02—Compounds containing any of the groups, e.g. carbazates
- C07C281/04—Compounds containing any of the groups, e.g. carbazates the other nitrogen atom being further doubly-bound to a carbon atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/16—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/74—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/76—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/02—Compounds containing any of the groups, e.g. carbazates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
- C07C281/08—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/08—Acetic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Description
448 089
vändigagautoklavreaktionen och de för låga utbytena. ,o_ pdf*
Ett tredje förfarande (W.-Deuschel,_Helv. Chim. Acta 35, 1587
'(1952)) kondenserar en blandning av ättiksyraester och myrsy-
raester med alkoholfritt natriumalkoholat, som framställes av
pulvriserat natrium och alkohol i eter. På grund av användnin-
gen av natriumsuspensioner i eter ocb med hänsyn till de låga
utbytena är detta förfarande i bästa fall inskränkt till arbe-
ten i laboratorieskala,_men det är helt olämpligt för en tek-
_nisk tillverkning.
Föreliggande uppfinning har sålunda som uppgift att arbeta
fram ett förfarande, som medger en problemfri framställning
av acylhydrazoner av formylättiksyraester i högt utbyte med
endast ett steg vid undvikande av formylättiksyraester-natri-
~ umsalt som mellansteg och är lämpligt för en teknisk framställ-
ning av denna substansklass.
Denna uppgift löses i enlighet med uppfinningen med hjälp av
ett förfarande för framställning av acylhydrazoner av formyl-
ättiksyraester med den allmänna formeln I "
H - c - caz - cooR1
N - NH ~ co - R2
”där R1 betecknar en Cieê -alkylrest och R2 en C -C -alkoxi-
6 1 4 e
rest eller en aminogrupp, vilket förfarande kännetecknas av
att man omsätter propiolsyraester med den allmänna formeln
H --c'= c - cooR1 g A' I II 1 A*
i vilken R1 har ovan angiven betydelse; med hydrazinderivat
' š-Z/.Ll
med den allmänna formeln
H N - NH - co - Rz ' l l III
2
g m'
_ -.-»>-
44% 089
. 3ghg V .. _ .._,
i vilken R2 har ovan angiven betydelse, i vattenhaltigt medium,Q
i,en C1-C4~alkohol eller i en blandning av vatten med en C1-C4-
alkohol vid temperaturer av OO till 5000. '
Förfarandet enligt uppfinningen begagnar sig således av lätt*
tillgängliga utgångsmaterial och möjliggör en tekniskt enkel och
riskfri framställning av de önskade slutprodukterna i höga utbyten.7
Syntesen av acylhydrazonerna med formel I sker utgående från oro-"
piolsyraester med formel II genom omsättning med ekvimolära mäng~
der av hydrazinderivat med formel III i vattenhaltigt medium, i
en C1:C4-alkohol eller i en blandning av vatten och en C1-C4fal~>
kohol. Lämpligen tillföres propiolsyraestern portionsvis eller
också utspädd med en C1-C4-alkohol till den med vatten eller en
C,-C4-alkohol utspädda lösningen av hydrazinkomponenten. Härvid
kan blandningsförhâllandet alkohol/vatten variera inom vida grän-
ser, i det att såväl alkohol enbart som även vatten enbart kan
komma till användning. Företrädesvis kan viktförhållandet alkohol/
vatten uppgå till 1:1. Tillsättningen av de i reaktionen deltagan-_
de ämnena kan även företagas i omvänd ordningsföljd, Reaktionen
sker vid temperaturer av OOC till 50oC. I
Som C1-C4-alkoholer kan exempelvis nämnas: metanol, etanol, pro-
panol, isopropanol, butanol, s-butanol, t~butanol.
Efter genomförd reaktion kan de i regel fasta reaktionsproduk-
terna isoleras i form av färglösa kristaller genom filtrering,
genom utfrysning eller genom borttagning av lösningsmedlet. De
kan lätt omkristalliseras ur lämpliga organiska lösningsmedel,
som t.ex. ketoner, alkoholer, nitriler, estrar, etrar och klore-
rade kolväten, t.ex. aceton, metanol, etanol, acetonitril, ät-
tikester, diisopropyleter och kloroform, och är stabila vid
rumstemperatur. Föreningarna erhålles emellertid vanligen i så
hög renhet, att de kan omsättas vidare i omkristalliserad form.
Följande exempel är ägnade att belysa förfarandet enligt upp»
finningen.
Exempel 1'i
44sgos9
ȁS
Framställning av formylättiksyraetylester-semikarbazon
""C3-semikarbazonoepropionsyraetylester)
I en trehalsad 100 ml rundkolv med omrörare_Qch termometer
löstes 11,15 g (0Q1.mol) Semikarbazidhydroklorid i 10 ml vat-
ten, försattes med 10,0 g (051 mol) kalíumvätekarbonat och
utspäddes därefter med 10 ml etanol. Härtill droppar man i,
9,8 g (0¿1 mol) propiolsyraetylester inom loppet av 5 minu-
ter. Reaktionstemperaturen hölls under U timmar vid ca 5000,
,varvíd så småningom en tjock kristallgröthbildades. Sedan
denna fått stå över natt kylda man í isbad och spådde den
med 10 ml vatten. Kristallerna sögs av, tvättades med 10 ml
vatten och tqrkades iavakuum vid uo°c till konstant vikt,
Utbyteze 0 16¿2 g É 95,5 % av det teoretiska utbytet
smältpunkta 1u7l- 1u8°c 0
Tunnskiktskromatografi: rörlig fas = ättikester/kloroform 1:1
Rf-värde: 0;110
-Analys: ia. Beräknat c u1,62 % -H 6,Mo % N 2u,26 %
Famnet c H1,7o %- H 6,ho.% N 23,89 %
Exempel 2'
Framställning av formylättiksyraetylester-etoxikarbonyl~
hydrazon (Beetoxikarbonylhydrazono-propionsyraëtylester)
I en trehalsad 250 ml rundkolv med omrörare och termometer
löstes U1,6 g (0¿Ä mol) hydrazinomyrsyraetylester i 120 ml
etanol och försattes med 59,2 g (0,U mol) propíolsyraetyl-
ester. Temperaturen steg därvid ti1l_30°C och hölls konstant
í ytterligare 3 timmar. Sedan reaktionsblandningen fått stå
över natt vid rumstemperatur indunstades den i vakuum vid
UCOC. Den gula, oljiga återstoden kristalliserade vid riv-
ning. Kristallerna pulvriserades.med en blandning av 60 ml. 7 4¿¿ Å
11-9,
_ isopropyleter och 60 ml cyklohexan, tvättades med 100 ml
cyklohexan och torkades i vakuum vid rumstemperatur till kon-
stant víkt. ' "
448 B89
Utbyte: 71,2 g = 88,0 % av det teoretiska
smä1tpunkt= 6M - 66°c.
Tunnskiktskromatografi; rörlig fas = ättikester/kloroforfi 1:1
¶ Rf-värae=lo,36o
Analys: ' Beräknat C ü7,52 % H 6,98 % N 13,86 %
Funnet c u7,21 % H 6,77 % N 1u,o8 %
ucbytëåuü
De vid förfarandet erhållna produkterna är tekniskfi värde-
'fulla utgångsprodukter för framställningen av biocíder, t.ex;
'1,2,3-tiadíazol-5-karboxylsyraderivat och 1,2,3-tíadiazol-
-5-yl-karbamider.
Claims (1)
- 448 089 Patentkrav Sätt att framställa acjlhydrazoner av fornylättiksyraester-med den allmänna formeln ' V -H-o-CHZZ-coofg in to I I N-NH-co-Rz där R1 betecknar en C1-C6-alkylrest och R2 en C¿-C4-alkoxirestf elle; en aminogruPP: ak ä n n e t e c k n a t av att man omsät- ter propiolsyraester med den allmänna formeln H - c. ä c - cooR1 - II i vilken R1 har ovan angiven betydelse, med hyárazinderivat med den allmänna formeln' ngn - ¶NH - co - 112 I III i vilken R2 har ošan angiven betydelse, i vattenhaltigt medium, i en Ci-C4-alkohol eller i en blandning av vatten med en C1-C4~ -alkohol vid temperaturer av OO till 5000. .eg I ., . " 'RÅM
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792945406 DE2945406A1 (de) | 1979-11-07 | 1979-11-07 | Verfahren zur herstellung von acylhydrazonen des formylessigsaeureesters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8007042L SE8007042L (sv) | 1981-05-08 |
| SE448089B true SE448089B (sv) | 1987-01-19 |
Family
ID=6085642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8007042A SE448089B (sv) | 1979-11-07 | 1980-10-08 | Sett att framstella acylhydrazoner av formylettiksyraester |
Country Status (37)
| Country | Link |
|---|---|
| US (1) | US4289897A (sv) |
| JP (1) | JPS5811434B2 (sv) |
| AR (1) | AR225194A1 (sv) |
| AT (1) | AT373869B (sv) |
| AU (1) | AU534907B2 (sv) |
| BE (1) | BE886085A (sv) |
| BG (1) | BG31494A3 (sv) |
| BR (1) | BR8006947A (sv) |
| CA (1) | CA1134382A (sv) |
| CH (1) | CH645612A5 (sv) |
| CS (1) | CS215074B2 (sv) |
| DD (1) | DD154099A5 (sv) |
| DE (1) | DE2945406A1 (sv) |
| DK (1) | DK469580A (sv) |
| EG (1) | EG14677A (sv) |
| ES (1) | ES8106488A1 (sv) |
| FI (1) | FI803393L (sv) |
| FR (1) | FR2469396A1 (sv) |
| GB (1) | GB2062632B (sv) |
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| IL (1) | IL61412A (sv) |
| IT (1) | IT1149845B (sv) |
| LU (1) | LU82915A1 (sv) |
| NL (1) | NL8005368A (sv) |
| NZ (1) | NZ195277A (sv) |
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| PL (1) | PL126806B1 (sv) |
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| SU (1) | SU959625A3 (sv) |
| TR (1) | TR20961A (sv) |
| YU (1) | YU40609B (sv) |
| ZA (1) | ZA806906B (sv) |
| ZW (1) | ZW27080A1 (sv) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4297448A (en) * | 1979-10-17 | 1981-10-27 | Ford Motor Company | Coating composition of aminoplast, hydroxy polymers and vinylic monomers |
| US10743535B2 (en) | 2017-08-18 | 2020-08-18 | H&K Solutions Llc | Insecticide for flight-capable pests |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3886211A (en) * | 1968-12-10 | 1975-05-27 | Ciba Geigy Corp | Carboxylic acid hydrazide derivatives |
| US4236017A (en) * | 1979-07-27 | 1980-11-25 | Montedison S.P.A., | Process for synthesizing 2-substituted semicarbazones and carbalkoxy hydrazones |
-
1979
- 1979-11-07 DE DE19792945406 patent/DE2945406A1/de active Granted
- 1979-11-07 ZA ZA00806906A patent/ZA806906B/xx unknown
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1980
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- 1980-10-01 YU YU2505/80A patent/YU40609B/xx unknown
- 1980-10-03 BG BG049245A patent/BG31494A3/xx unknown
- 1980-10-07 IT IT25153/80A patent/IT1149845B/it active
- 1980-10-08 SE SE8007042A patent/SE448089B/sv not_active IP Right Cessation
- 1980-10-08 ES ES495742A patent/ES8106488A1/es not_active Expired
- 1980-10-08 CH CH752280A patent/CH645612A5/de not_active IP Right Cessation
- 1980-10-09 SU SU802990891A patent/SU959625A3/ru active
- 1980-10-10 CS CS806876A patent/CS215074B2/cs unknown
- 1980-10-10 US US06/196,150 patent/US4289897A/en not_active Expired - Lifetime
- 1980-10-10 AR AR282830A patent/AR225194A1/es active
- 1980-10-16 NZ NZ195277A patent/NZ195277A/xx unknown
- 1980-10-21 RO RO102391A patent/RO81343B/ro unknown
- 1980-10-27 AU AU63720/80A patent/AU534907B2/en not_active Ceased
- 1980-10-29 BR BR8006947A patent/BR8006947A/pt unknown
- 1980-10-29 FI FI803393A patent/FI803393L/fi not_active Application Discontinuation
- 1980-11-03 GB GB8035238A patent/GB2062632B/en not_active Expired
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- 1980-11-04 JP JP55153973A patent/JPS5811434B2/ja not_active Expired
- 1980-11-04 PL PL1980227653A patent/PL126806B1/pl unknown
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- 1980-11-05 DK DK469580A patent/DK469580A/da not_active Application Discontinuation
- 1980-11-05 PT PT72022A patent/PT72022B/pt unknown
- 1980-11-05 EG EG679/80A patent/EG14677A/xx active
- 1980-11-06 FR FR8023714A patent/FR2469396A1/fr active Granted
- 1980-11-06 CA CA000364094A patent/CA1134382A/en not_active Expired
- 1980-11-06 LU LU82915A patent/LU82915A1/de unknown
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