PL51202B1 - - Google Patents
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- Publication number
- PL51202B1 PL51202B1 PL104112A PL10411264A PL51202B1 PL 51202 B1 PL51202 B1 PL 51202B1 PL 104112 A PL104112 A PL 104112A PL 10411264 A PL10411264 A PL 10411264A PL 51202 B1 PL51202 B1 PL 51202B1
- Authority
- PL
- Poland
- Prior art keywords
- group
- wzdr
- phosgene
- general formula
- hydrogen
- Prior art date
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- 238000000034 method Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 1
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 claims 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- -1 5-nitroisoindoline-2-carboxylic acid chloride Chemical compound 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
C14H18N20 (230,30); N (z wyliczenia) — 12,16%; N (znaleziony) 40 - 11,94%.Przyklad-X. Do mieszaniny skladajacej sie z 4,52 g dwuetyloaminy, 6,26 g trójetyloaminy i 50 cm3 acetonu wkrapla sie podczas mieszania w temperaturze pokojowej w ciagu. 20 minut roz- 45 twór 14,0 g chlorku kwasu 5-nitroizoindolino-2- karboksylowego (temperatura topnienia 120°C), otrzymanego jak w przykladzie IX, w 125 cm3 acetonu i ogrzewa do wrzenia w ciagu 2 godzin.Po oziebieniu roztwór odsacza sie od chlorowo- 50 dorku trójetyloaminy, przesacz zadaje 50 cm3 roz¬ cienczonego kwasu solnego i wieksza czesc roz¬ puszczalnika oddestylowuje pod próznia. Z po¬ zostalego roztworu wykrystalizowuje surowy dwu- etyloamid kwasu 5-nitroizoindolino-2-karboksylo- 55 wego, który w celu ^czyszczenia przekrystalizo¬ wuje sie z etanolu i przemywa na frycie (stop drobnozmielonych krzemianów) 300 cm3 wody.Wydajnosc: 13,6 g = 83,7% teorii; temperatura topnienia 90—91°C (benzen/eter). C13H17N303 (263,29); go N (z wyliczenia) — 15,96%; N (znaleziony) — 15,60%.Przez katalityczne uwodornienie otrzymuje sie dwuetyloamid kwasu 5-aminoizoindolino-2-karbo- ksylowego w postaci chlorowodorku. Temperatura ^ topnienia niezupelnie oczyszczonego produktu 3551202 okolo 178—188°C (etanol/eter), C]3H20ClN3O (269,77); N (z wyliczenia) — 15,57%; N (znaleziony) — 15,24%. PL
Claims (1)
1. Zastrzezenie patentowe Sposób wytwarzania amidów kwasu izoindo- lino-2-karboksylowego o ogólnym wzorze 1, w któ¬ rym Y oznacza atom wodoru, grupe nitrowa lub grupe aminowa, a Ri i (albo) R2 oznacza wodór, reszty alkilowa, cykloalkilowa, aryloalkilowa albo arylowa, ewentualnie podstawione lub tworzace 6 czlon heterocyklicznego pierscienia, znamienny tym, ze izoindoline o ogólnym wzorze 2, w którym Y oznacza wodór albo grupe nitrowa, wprowadza sie w reakcje izocyjanianami, z chlorkami kwasu 5 karbaminowego albo z aktywnymi pochodnymi mocznika, zwlaszcza z nitromocznikiem lub z fos¬ genem, przy czym produkt reakcji z fosgenem poddaje sie aminolizie, a aromatyczna grupe ni¬ trowa ewentualnie redukuje sie do grupy 10 aminowej.KI. 12p, 2 51202 MKP C 07 d N-CO -N R. Wzdr/ Wzdr 2 Czst. :am. 514 z dn. 8.2.66. 270 egz. PL
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL51202B1 true PL51202B1 (pl) | 1966-02-25 |
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