DD155901A1 - Verfahren zur herstellung von n-/3-(1'-3"-oxapentamethylenaminoaethylidenamino)2,4,6-trijodbenzoyl/-beta-amino-alpha-methylpropionsaeure - Google Patents

Verfahren zur herstellung von n-/3-(1'-3"-oxapentamethylenaminoaethylidenamino)2,4,6-trijodbenzoyl/-beta-amino-alpha-methylpropionsaeure Download PDF

Info

Publication number: DD155901A1
Authority: DD; German Democratic Republic
Prior art keywords: amino; triiodobenzoyl; formula; methylpropionitrile; nitrile
Prior art date: 1980-01-04

Application number

DD22672780A

Other languages

German (de)

English (en)

Inventor

Josef Wieser

Josef Krieger

Original Assignee

Chemie Linz 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.)

1980-01-04

Filing date

1980-12-30

Publication date

1982-07-14

1980-12-30 Application filed by Chemie Linz Ag filed Critical Chemie Linz Ag

1982-07-14 Publication of DD155901A1 publication Critical patent/DD155901A1/de

Links

QCHPKSFMDHPSNR-UHFFFAOYSA-N 3-aminoisobutyric acid Chemical compound NCC(C)C(O)=O QCHPKSFMDHPSNR-UHFFFAOYSA-N 0.000 title 1
238000004519 manufacturing process Methods 0.000 title 1
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 33
150000002825 nitriles Chemical class 0.000 claims abstract description 29
KYWXRBNOYGGPIZ-UHFFFAOYSA-N 1-morpholin-4-ylethanone Chemical compound CC(=O)N1CCOCC1 KYWXRBNOYGGPIZ-UHFFFAOYSA-N 0.000 claims abstract description 23
238000000034 method Methods 0.000 claims abstract description 21
239000002253 acid Substances 0.000 claims abstract description 16
238000002360 preparation method Methods 0.000 claims abstract description 10
239000002904 solvent Substances 0.000 claims abstract description 7
230000002378 acidificating effect Effects 0.000 claims abstract description 4
-1 3-amino-2,4,6-triiodobenzoyl Chemical group 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
238000001704 evaporation Methods 0.000 claims description 5
230000008020 evaporation Effects 0.000 claims description 5
239000000376 reactant Substances 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
239000003929 acidic solution Substances 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
238000007127 saponification reaction Methods 0.000 abstract description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
239000000243 solution Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000006227 byproduct Substances 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
150000001875 compounds Chemical class 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000000746 purification Methods 0.000 description 6
238000001816 cooling Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
239000003610 charcoal Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 4
VVODXPFIWOSTQB-UHFFFAOYSA-N 3-amino-2,4,6-triiodobenzoyl chloride Chemical compound NC1=C(I)C=C(I)C(C(Cl)=O)=C1I VVODXPFIWOSTQB-UHFFFAOYSA-N 0.000 description 3
GDIMNXJSMJSDSB-UHFFFAOYSA-N 3-amino-2-methylpropanenitrile Chemical compound NCC(C)C#N GDIMNXJSMJSDSB-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000002585 base Substances 0.000 description 3
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
150000007513 acids Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000004140 cleaning Methods 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
210000000232 gallbladder Anatomy 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
235000010678 Paulownia tomentosa Nutrition 0.000 description 1
240000002834 Paulownia tomentosa Species 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
210000000013 bile duct Anatomy 0.000 description 1
239000012267 brine Substances 0.000 description 1
OUMSIYHSIIRHKR-LSHDLFTRSA-N chembl2104832 Chemical compound OC(=O)C(C)CNC(=O)C1=C(I)C=C(I)C(\N=C(/C)N2CCOCC2)=C1I OUMSIYHSIIRHKR-LSHDLFTRSA-N 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000002872 contrast media Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000037406 food intake Effects 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000002463 imidates Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229950003310 iomorinic acid Drugs 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

DD22672780A 1980-01-04 1980-12-30 Verfahren zur herstellung von n-/3-(1'-3"-oxapentamethylenaminoaethylidenamino)2,4,6-trijodbenzoyl/-beta-amino-alpha-methylpropionsaeure DD155901A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19803000215 DE3000215A1 (de)	1980-01-04	1980-01-04	Verfahren zur herstellung von n-(3-(1'-3"-oxapentamethylenamino-aethylidenamino)-2,4,6-trijodbenzoyl)- (beta) - amino- (alpha) -methylpropionsaeure

Publications (1)

Publication Number	Publication Date
DD155901A1 true DD155901A1 (de)	1982-07-14

Family

ID=6091548

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD22672780A DD155901A1 (de)	1980-01-04	1980-12-30	Verfahren zur herstellung von n-/3-(1'-3"-oxapentamethylenaminoaethylidenamino)2,4,6-trijodbenzoyl/-beta-amino-alpha-methylpropionsaeure

Country Status (10)

Country	Link
CS (1)	CS216545B2 (cs)
DD (1)	DD155901A1 (cs)
DE (1)	DE3000215A1 (cs)
ES (1)	ES498238A0 (cs)
HU (1)	HU180185B (cs)
PL (1)	PL127295B1 (cs)
PT (1)	PT72221B (cs)
RO (1)	RO81056A (cs)
SU (1)	SU980618A3 (cs)
YU (1)	YU309780A (cs)

1980
- 1980-01-04 DE DE19803000215 patent/DE3000215A1/de not_active Withdrawn
- 1980-12-08 YU YU309780A patent/YU309780A/xx unknown
- 1980-12-18 PT PT7222180A patent/PT72221B/pt unknown
- 1980-12-26 SU SU803221254A patent/SU980618A3/ru active
- 1980-12-28 HU HU312780A patent/HU180185B/hu unknown
- 1980-12-30 RO RO80103041A patent/RO81056A/ro unknown
- 1980-12-30 DD DD22672780A patent/DD155901A1/de unknown
- 1980-12-30 ES ES498238A patent/ES498238A0/es active Granted
1981
- 1981-01-02 PL PL22904181A patent/PL127295B1/pl unknown
- 1981-01-04 CS CS4981A patent/CS216545B2/cs unknown

Also Published As

Publication number	Publication date
RO81056B (ro)	1983-05-30
HU180185B (en)	1983-02-28
PT72221A (en)	1981-01-01
SU980618A3 (ru)	1982-12-07
DE3000215A1 (de)	1981-07-09
ES8201148A1 (es)	1981-12-01
PL229041A1 (cs)	1981-10-16
YU309780A (en)	1983-01-21
ES498238A0 (es)	1981-12-01
PL127295B1 (en)	1983-10-31
CS216545B2 (en)	1982-11-26
RO81056A (ro)	1983-06-01
PT72221B (en)	1981-11-02

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