CS216545B2 - Method of production of the n-+l 3-+l 1-3"- oxapentamethylenaminoethylidenamino + p -2,4,6-triiodbenzoyl + p-beta-amino-alpfa methylpropion acid - Google Patents
Method of production of the n-+l 3-+l 1-3"- oxapentamethylenaminoethylidenamino + p -2,4,6-triiodbenzoyl + p-beta-amino-alpfa methylpropion acid Download PDFInfo
- Publication number
- CS216545B2 CS216545B2 CS4981A CS4981A CS216545B2 CS 216545 B2 CS216545 B2 CS 216545B2 CS 4981 A CS4981 A CS 4981A CS 4981 A CS4981 A CS 4981A CS 216545 B2 CS216545 B2 CS 216545B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- amino
- triiodobenzoyl
- nitrile
- acid
- acetylmorpholine
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 46
- 150000002825 nitriles Chemical class 0.000 claims description 27
- KYWXRBNOYGGPIZ-UHFFFAOYSA-N 1-morpholin-4-ylethanone Chemical compound CC(=O)N1CCOCC1 KYWXRBNOYGGPIZ-UHFFFAOYSA-N 0.000 claims description 22
- -1 3-amino-2,4,6-tri-iodobenzyl Chemical group 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 238000007127 saponification reaction Methods 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 239000006227 byproduct Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000007858 starting material 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
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003929 acidic solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 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 2
- QCHPKSFMDHPSNR-UHFFFAOYSA-N 3-Amino-2-methylpropanoic acid Natural products NCC(C)C(O)=O QCHPKSFMDHPSNR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 210000000013 bile duct Anatomy 0.000 description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JQULXIOYDDCNGR-UHFFFAOYSA-N 2-amino-2-methylpropanenitrile Chemical compound CC(C)(N)C#N JQULXIOYDDCNGR-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 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
- YNTQKXBRXYIAHM-UHFFFAOYSA-N azanium;butanoate Chemical compound [NH4+].CCCC([O-])=O YNTQKXBRXYIAHM-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003610 charcoal 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
- 238000009606 cholecystography Methods 0.000 description 1
- 238000004140 cleaning Methods 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
- 150000002148 esters Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 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
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids 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
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure 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)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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 |
|---|---|
| CS216545B2 true CS216545B2 (en) | 1982-11-26 |
Family
ID=6091548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS4981A CS216545B2 (en) | 1980-01-04 | 1981-01-04 | Method of production of the n-+l 3-+l 1-3"- oxapentamethylenaminoethylidenamino + p -2,4,6-triiodbenzoyl + p-beta-amino-alpfa methylpropion acid |
Country Status (10)
| Country | Link |
|---|---|
| CS (1) | CS216545B2 (ro) |
| DD (1) | DD155901A1 (ro) |
| DE (1) | DE3000215A1 (ro) |
| ES (1) | ES8201148A1 (ro) |
| HU (1) | HU180185B (ro) |
| PL (1) | PL127295B1 (ro) |
| PT (1) | PT72221B (ro) |
| RO (1) | RO81056A (ro) |
| SU (1) | SU980618A3 (ro) |
| YU (1) | YU309780A (ro) |
-
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 ES ES498238A patent/ES8201148A1/es not_active Expired
- 1980-12-30 DD DD22672780A patent/DD155901A1/de unknown
-
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 |
|---|---|
| PT72221A (en) | 1981-01-01 |
| SU980618A3 (ru) | 1982-12-07 |
| YU309780A (en) | 1983-01-21 |
| ES498238A0 (es) | 1981-12-01 |
| ES8201148A1 (es) | 1981-12-01 |
| RO81056B (ro) | 1983-05-30 |
| DE3000215A1 (de) | 1981-07-09 |
| HU180185B (en) | 1983-02-28 |
| PL127295B1 (en) | 1983-10-31 |
| PT72221B (en) | 1981-11-02 |
| RO81056A (ro) | 1983-06-01 |
| PL229041A1 (ro) | 1981-10-16 |
| DD155901A1 (de) | 1982-07-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0371431B2 (ro) | ||
| AU638688B2 (en) | Process for the preparation of 2,4,6-triiodo-5-amino-isophthalamide compounds | |
| US20040171872A1 (en) | Purification of 2-nitro-4-methylsuphonyblenzoic acid | |
| EP2723709A1 (en) | Manufacture of a triiodinated contrast agent | |
| CS216545B2 (en) | Method of production of the n-+l 3-+l 1-3"- oxapentamethylenaminoethylidenamino + p -2,4,6-triiodbenzoyl + p-beta-amino-alpfa methylpropion acid | |
| DE1176660B (de) | Verfahren zur Herstellung von triaryl-substituierten Imidazolinonen-4(5) | |
| FI69457B (fi) | N-(3-(1'-3"-oxapentametylenamino-etylidenamino)-2,4,6-trijodbenzoy1)-beta-amino-alfa-metylpropionitril och foerfarande foer dess framstaellning | |
| JPH0597782A (ja) | 塩酸ベバントロールの製造方法 | |
| DE2416355A1 (de) | Direkte synthese von dopaminaminosaeureamiden | |
| US4247693A (en) | Process for preparing 2,4,5,6-tetraaminopyrimidine sulfate | |
| US3202712A (en) | 1-cyclohexene-4-bis (omicron-chlorobenzylaminomethyl) and derivatives | |
| SU567402A3 (ru) | Способ получени производных хинолина или их солей | |
| WO2001096316A1 (de) | Verfahren zur herstellung von substituierten 5-amino-n-phenyl-1,2,4-triazol-3-sulfonamiden | |
| EP0408654A1 (en) | METHOD FOR PRODUCING 2,4,6-TRIIODO-5-AMINO-N-ALKYL-ISOPHTHALIC ACID. | |
| SU1117299A1 (ru) | Способ получени 2-аминотиазолина | |
| AT366381B (de) | Verfahren zur herstellung von n-(3-(1'-3''oxapentamethylenamino-aethylidenamino)-2,4,6- | |
| JPH11511439A (ja) | Ｎ−カルボキシメチレン−４−クロロ−アントラニル酸並びにそのジアルキルエステルの製造方法 | |
| SU372227A1 (ru) | БИБЛИОТЕКАвеществ АН Узбекской ССР | |
| SU286636A1 (ru) | Способ получения производных 2,4,6-трийод- бензойной кислоты | |
| JPH0559027A (ja) | ２−メルカプト−ベンゾチアゾールの製法 | |
| JPH08269020A (ja) | ５−置換ジヒドロウラシル類の製造法 | |
| JPH0782237A (ja) | β−クロロエタンスルホン酸ソーダの精製方法 | |
| JPS6343395B2 (ro) | ||
| BE546776A (ro) | ||
| CS269038B1 (sk) | SpQsob výroby izopropylamidu kyseliny antranilovej |