CH392484A - Verfahren zur Herstellung von aromatischen ortho-disubstituierten Säure-Amiden - Google Patents

Verfahren zur Herstellung von aromatischen ortho-disubstituierten Säure-Amiden

Info

Publication number: CH392484A
Authority: CH; Switzerland
Prior art keywords: sep; preparation; amine; acid amides; formula
Prior art date: 1959-02-07

Application number

CH130860A

Other languages

German (de)

English (en)

Inventor

Jaakko Juhani Dr Techn Hukki

Juhani Honkanen Erkki

Original Assignee

Laaketehdas Orion Oy

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.)

1959-02-07

Filing date

1960-02-05

Publication date

1965-05-31

1960-02-05 Application filed by Laaketehdas Orion Oy filed Critical Laaketehdas Orion Oy

1965-05-31 Publication of CH392484A publication Critical patent/CH392484A/de

Links

238000000034 method Methods 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title claims description 11
125000003118 aryl group Chemical group 0.000 title claims description 9
150000001408 amides Chemical class 0.000 title claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000001302 tertiary amino group Chemical group 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims 6
125000005843 halogen group Chemical group 0.000 claims 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 2
-1 aromatic acid halide Chemical class 0.000 claims 1
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical group CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical group 0.000 claims 1
QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 8
239000002253 acid Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
JJRYPZMXNLLZFH-GFUIURDCSA-N (6R)-dehydrovomifoliol Chemical compound CC(=O)\C=C\[C@]1(O)C(C)=CC(=O)CC1(C)C JJRYPZMXNLLZFH-GFUIURDCSA-N 0.000 description 2
JAVBBFXUGDCHLZ-UHFFFAOYSA-N 1-$l^{1}-oxidanylpropane Chemical compound CCC[O] JAVBBFXUGDCHLZ-UHFFFAOYSA-N 0.000 description 2
ZOAMZFNAPHWBEN-UHFFFAOYSA-N 2-$l^{1}-oxidanylpropane Chemical compound CC(C)[O] ZOAMZFNAPHWBEN-UHFFFAOYSA-N 0.000 description 2
CHSAZBMOBSHGFV-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)phenyl]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=C(CCO)C=C1 CHSAZBMOBSHGFV-UHFFFAOYSA-N 0.000 description 2
SVAGJHVIBWWSLV-UHFFFAOYSA-N 3,6-ditert-butyl-4-chlorocyclohexa-3,5-diene-1,2-dione Chemical compound CC(C)(C)C1=CC(Cl)=C(C(C)(C)C)C(=O)C1=O SVAGJHVIBWWSLV-UHFFFAOYSA-N 0.000 description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
QOOQLKSEGVNYLA-UHFFFAOYSA-N 1-$l^{1}-oxidanylbutane Chemical compound CCCC[O] QOOQLKSEGVNYLA-UHFFFAOYSA-N 0.000 description 1
FFFIRKXTFQCCKJ-UHFFFAOYSA-N 2,4,6-trimethylbenzoic acid Chemical compound CC1=CC(C)=C(C(O)=O)C(C)=C1 FFFIRKXTFQCCKJ-UHFFFAOYSA-N 0.000 description 1
HCBHQDKBSKYGCK-UHFFFAOYSA-N 2,6-dimethylbenzoic acid Chemical compound CC1=CC=CC(C)=C1C(O)=O HCBHQDKBSKYGCK-UHFFFAOYSA-N 0.000 description 1
OITNBJHJJGMFBN-UHFFFAOYSA-N 4-(chloromethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(CCl)C=C1 OITNBJHJJGMFBN-UHFFFAOYSA-N 0.000 description 1
NENRPNVWXFRNKL-UHFFFAOYSA-N 4-ethoxy-2,6-dimethylbenzoyl chloride Chemical compound CCOC1=CC(C)=C(C(Cl)=O)C(C)=C1 NENRPNVWXFRNKL-UHFFFAOYSA-N 0.000 description 1
GFWRERVOFRPXKB-UHFFFAOYSA-N 4-methoxy-2,6-dimethylbenzoic acid Chemical compound COC1=CC(C)=C(C(O)=O)C(C)=C1 GFWRERVOFRPXKB-UHFFFAOYSA-N 0.000 description 1
VCZNNAKNUVJVGX-UHFFFAOYSA-N 4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C=C1 VCZNNAKNUVJVGX-UHFFFAOYSA-N 0.000 description 1
CJKRXEBLWJVYJD-UHFFFAOYSA-N N,N'-diethylethylenediamine Chemical compound CCNCCNCC CJKRXEBLWJVYJD-UHFFFAOYSA-N 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
150000003842 bromide salts Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH130860A 1959-02-07 1960-02-05 Verfahren zur Herstellung von aromatischen ortho-disubstituierten Säure-Amiden CH392484A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FI22759		1959-02-07

Publications (1)

Publication Number	Publication Date
CH392484A true CH392484A (de)	1965-05-31

Family

ID=8503813

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH130860A CH392484A (de)	1959-02-07	1960-02-05	Verfahren zur Herstellung von aromatischen ortho-disubstituierten Säure-Amiden

Country Status (6)

Country	Link
AT (1)	AT218513B (da)
BE (1)	BE587137A (da)
CH (1)	CH392484A (da)
DK (1)	DK95874C (da)
FI (1)	FI33631A (da)
GB (1)	GB877846A (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH488691A (de) *	1967-10-20	1970-04-15	Eprova Ag	Verfahren zur Herstellung von neuen Butoxy-dimethylbenzamiden

1959
- 1959-02-07 FI FI33631D patent/FI33631A/fi unknown
1960
- 1960-01-28 AT AT66460A patent/AT218513B/de active
- 1960-01-28 GB GB3094/60A patent/GB877846A/en not_active Expired
- 1960-02-01 BE BE587137A patent/BE587137A/fr unknown
- 1960-02-03 DK DK40160A patent/DK95874C/da active
- 1960-02-05 CH CH130860A patent/CH392484A/de unknown

Also Published As

Publication number	Publication date
GB877846A (en)	1961-09-20
FI33631A (fi)	1963-11-11
DK95874C (da)	1963-05-06
AT218513B (de)	1961-12-11
BE587137A (fr)	1960-05-30

Publication	Publication Date	Title
DE2429745C3 (de)	1981-02-19	Verfahren zur Herstellung von Triacetonamin
CH392484A (de)	1965-05-31	Verfahren zur Herstellung von aromatischen ortho-disubstituierten Säure-Amiden
CH343388A (de)	1959-12-31	Verfahren zur Herstellung neuer Amide
DE2602846C2 (de)	1986-02-13	Verfahren zur Herstellung von 2-(2-Thienyl)äthylaminen
DE1620128C3 (de)	1973-10-04	N Aminoalkyl 2 phenoxy 2 phenyl acetamide, deren Saureadditionssalze, sowie Verfahren zu ihrer Herstellung
DE812669C (de)	1951-09-03	Verfahren zur Herstellung von 1-Aryl-cyclopenten-(3)-1-nitrilen, deren Carbonsaeuren, deren basischen Estern und Amiden und deren Salzen
DE850748C (de)	1952-09-29	Verfahren zur Herstellung von Piperazin-1-carbonsaeureamiden
DE2449285A1 (de)	1976-04-22	Verfahren zur herstellung von chlorierten aromatischen aminen
CH356121A (de)	1961-08-15	Verfahren zur Herstellung von N-monosubstituierten Amiden vona-Aminoalkyl-a-phenyl-essigsäuren
AT238186B (de)	1965-01-25	Verfahren zur Herstellung neuer Pyrrolidinverbindungen
AT311338B (de)	1973-11-12	Verfahren zum Herstellen eines neuen Imidazolinderivates und seiner Salze
AT226679B (de)	1963-04-10	Verfahren zur Herstellung von neuen o-Phenylendiaminen
DE950550C (de)	1956-10-11	Verfahren zur Herstellung von basisch substituierten Phenylcycloalkenylpropanolen
AT238182B (de)	1965-01-25	Verfahren zur Herstellung neuer Pyrrolidinverbindungen
AT238181B (de)	1965-01-25	Verfahren zur Herstellung neuer Pyrrolidinverbindungen
DE1518652A1 (de)	1969-04-10	Verfahren zur Herstellung von pharmazeutisch wirksamen Derivaten des 2-Aminoindans
AT260914B (de)	1968-03-25	Verfahren zur Herstellung von neuen α-(Aminoalkoxyphenyl)-α'-nitrostilbenen und deren Säureadditionssalzen bzw. quaternären Ammoniumverbindungen
DE2714255A1 (de)	1978-10-05	Verfahren zur herstellung von m-aminophenolen und deren verwendung
AT258264B (de)	1967-11-10	Verfahren zur Herstellung von 5-(3'-Methylaminopropyl)-5H-dibenzo[a,d] cyclohepten
AT243248B (de)	1965-10-25	Verfahren zur Herstellung von α-n-Propylamino-2-methylpropionanilid
DE1199777B (de)	1965-09-02	Verfahren zur Herstellung von 2-Chlor-4-azaphenthiazinderivaten
CH349618A (de)	1960-10-31	Verfahren zur Herstellung von neuen Aminoessigsäure-aryliden
DE2201804A1 (de)	1972-07-27	Antiarrhythmische Phenylaethylbenzylamine
DE1137439B (de)	1962-10-04	Verfahren zur Herstellung von substituierten Morpholinen
DE1213851B (de)	1966-04-07	Verfahren zur Herstellung neuer pharmazeutisch wertvoller Thiophenverbindungen