CH396934A - Verfahren zur Herstellung basisch substituierter Malonsäuredinitrile - Google Patents

Verfahren zur Herstellung basisch substituierter Malonsäuredinitrile

Info

Publication number: CH396934A
Authority: CH; Switzerland
Prior art keywords: preparation; substituted; formamidinium; malonic acid; chloride
Prior art date: 1960-11-16

Application number

CH1219361A

Other languages

German (de)

English (en)

Inventor

Heinrich Dr Gold

Bayer Otto Dr Prof

Original Assignee

Bayer Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1960-11-16

Filing date

1961-10-21

Publication date

1965-08-15

1961-10-21 Application filed by Bayer Ag filed Critical Bayer Ag

1965-08-15 Publication of CH396934A publication Critical patent/CH396934A/de

Links

238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title description 7
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 24
-1 N, N, N ', N'-tetra-substituted formamidinium salt Chemical class 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
238000009835 boiling Methods 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
BPBLGCSAYMJJJW-UHFFFAOYSA-M dimethylaminomethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].CN(C)C=[N+](C)C BPBLGCSAYMJJJW-UHFFFAOYSA-M 0.000 description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
NMVVJCLUYUWBSZ-UHFFFAOYSA-N aminomethylideneazanium;chloride Chemical compound Cl.NC=N NMVVJCLUYUWBSZ-UHFFFAOYSA-N 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
QDLDLIRAAPKFKY-UHFFFAOYSA-M diethylaminomethylidene(diethyl)azanium;chloride Chemical compound [Cl-].CCN(CC)C=[N+](CC)CC QDLDLIRAAPKFKY-UHFFFAOYSA-M 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
239000000155 melt Substances 0.000 description 2
LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
HLAIWFQEDIRLGQ-UHFFFAOYSA-N 2-(diethylamino)propanedioic acid Chemical compound CCN(CC)C(C(O)=O)C(O)=O HLAIWFQEDIRLGQ-UHFFFAOYSA-N 0.000 description 1
OFEBXIWCDBEZGA-UHFFFAOYSA-N 2-(dimethylamino)propanedinitrile Chemical compound CN(C)C(C#N)C#N OFEBXIWCDBEZGA-UHFFFAOYSA-N 0.000 description 1
ULYPPRXOCVYILQ-UHFFFAOYSA-N 2-(dimethylamino)propanedioic acid Chemical compound CN(C)C(C(O)=O)C(O)=O ULYPPRXOCVYILQ-UHFFFAOYSA-N 0.000 description 1
RHHXOVPPWRMLIO-UHFFFAOYSA-N 2-piperidin-1-ylpropanedinitrile Chemical compound N#CC(C#N)N1CCCCC1 RHHXOVPPWRMLIO-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
229940005991 chloric acid Drugs 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
YECZTTHHUYWDCA-UHFFFAOYSA-N dimethyl-[1-(methylamino)ethylidene]azanium;chloride Chemical compound [Cl-].CNC(C)=[N+](C)C YECZTTHHUYWDCA-UHFFFAOYSA-N 0.000 description 1
XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002691 malonic acids Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
VKJPYCILSNITIZ-UHFFFAOYSA-N n'-phenylbenzenecarboximidamide;hydroiodide Chemical compound I.C=1C=CC=CC=1C(N)=NC1=CC=CC=C1 VKJPYCILSNITIZ-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CH1219361A 1960-11-16 1961-10-21 Verfahren zur Herstellung basisch substituierter Malonsäuredinitrile CH396934A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF32561A DE1128431B (de)	1960-11-16	1960-11-16	Verfahren zur Herstellung basisch substituierter Malonsaeuredinitrile

Publications (1)

Publication Number	Publication Date
CH396934A true CH396934A (de)	1965-08-15

Family

ID=7094685

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1219361A CH396934A (de)	1960-11-16	1961-10-21	Verfahren zur Herstellung basisch substituierter Malonsäuredinitrile

Country Status (4)

Country	Link
BE (1)	BE610352A (fr)
CH (1)	CH396934A (fr)
DE (1)	DE1128431B (fr)
GB (1)	GB939682A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN105985263B (zh) *	2015-02-03	2019-02-15	兰州大学	一种n,n-二取代氨基-丙二腈类化合物的合成方法

1960
- 1960-11-16 DE DEF32561A patent/DE1128431B/de active Pending
1961
- 1961-10-21 CH CH1219361A patent/CH396934A/de unknown
- 1961-10-25 GB GB3821861A patent/GB939682A/en not_active Expired
- 1961-11-16 BE BE610352A patent/BE610352A/fr unknown

Also Published As

Publication number	Publication date
GB939682A (en)	1963-10-16
DE1128431B (de)	1962-04-26
BE610352A (fr)	1962-03-16

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DE848503C (de)	1952-09-04	Verfahren zur Darstellung von basischen Estern
DE1161899B (de)	1964-01-30	Verfahren zur Herstellung von substituierten 1-Alkyl-piperidin-monocarbonsäureamiden und 1-Alkyl-pyrrolidin-2-monocarbonsäureamiden.
DE1146892B (de)	1963-04-11	Verfahren zur Herstellung von Orthoameisensaeuredialkylester-amiden
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AT228772B (de)	1963-08-12	Verfahren zur Herstellung von neuen basisch substituierten Malonsäuredinitrilen
CH396934A (de)	1965-08-15	Verfahren zur Herstellung basisch substituierter Malonsäuredinitrile
DE2220256A1 (de)	1973-11-08	N-(o- bzw. p-nitrobenzoyl)-sulfoximine, verfahren zu ihrer herstellung und verwendung derselben
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EP0224849B1 (fr)	1989-02-15	4-Mercaptobenzonitriles et leur procédé de préparation
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EP0257295B1 (fr)	1990-08-29	Chlorures d'acétyl (Z)-2-cyano-2-oximino et un procédé pour leur préparation
DD154100A5 (de)	1982-02-24	Verfahren zur herstellung von carbaminsaeureester-derivaten durch o-acylierung
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AT216520B (de)	1961-08-10	Verfahren zur Herstellung von neuen Derivaten des 2,3-Dimercaptochinoxalins
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AT289138B (de)	1971-04-13	Verfahren zur Herstellung von neuen substituierten Phenylcarbaminsäureestern von zyklischen Aminoalkoholen und ihren optischen Isomeren sowie ihren Säureadditionssalzen
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