CS225006B1 - The preparation of intermediate products for the synthesis of asymmetrica 1 quinoline single azo cianine colouring agents - Google Patents
The preparation of intermediate products for the synthesis of asymmetrica 1 quinoline single azo cianine colouring agents Download PDFInfo
- Publication number
- CS225006B1 CS225006B1 CS722179A CS722179A CS225006B1 CS 225006 B1 CS225006 B1 CS 225006B1 CS 722179 A CS722179 A CS 722179A CS 722179 A CS722179 A CS 722179A CS 225006 B1 CS225006 B1 CS 225006B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- preparation
- quinoline
- synthesis
- cianine
- asymmetrica
- Prior art date
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 230000015572 biosynthetic process Effects 0.000 title claims description 3
- 238000003786 synthesis reaction Methods 0.000 title claims description 3
- 239000004150 EU approved colour Substances 0.000 title 1
- 239000013067 intermediate product Substances 0.000 title 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 title 1
- 238000003756 stirring Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 239000000543 intermediate Substances 0.000 claims description 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 2
- -1 2-Imino-3 (gamma-sulfopropyl) -5-chloropyridinium Chemical compound 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- 229960003237 betaine Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Description
Vynález se týká způsobu přípravy nových meziproduktů obecného vzorce IThe present invention relates to a process for the preparation of novel intermediates of formula (I)
NH (i) (CH2)3so^ ve kterém R znamená vodíkový atom, halogen, které se používají k syntéze nesymetrických chinolinmonoazacyaninových barviv, používaných ke zlepšení fotografických vlastností materiálů a k syntéze delších chemických sloušenin, které obsahují dusíkový atom v polymethinovém řetězci.NH (i) (CH 2 ) 3 SO 4 wherein R represents a hydrogen atom, a halogen, used to synthesize unsymmetrical quinoline monoazacyanine dyes used to improve the photographic properties of materials and to synthesize longer chemical compounds containing a nitrogen atom in the polymethine chain.
Podstata způsobu přípravy meziproduktů obecného vzorce I podle vynálezu spočívá v tom že se 2-aminoderiváty příslušných heterocyklických bází obecného vzorce IIThe process for the preparation of the intermediates of the formula I according to the invention is characterized in that the 2-amino derivatives of the respective heterocyclic bases of the formula II
(IX) ve kterém R má výše uvedený význam, uvedou v reakci s 1,3-propansulfonem vzorce III ch2—ch2 (IX) in which R has the abovementioned meaning, are reacted with 1,3-propane of formula III CH 2 -CH 2
Χ(III)III (III)
ΟΗ, při teplotš 130 až 140 °C po dobu 1,5 až 2 hodin za míchání.Při, at a temperature of 130 to 140 ° C for 1.5 to 2 hours with stirring.
Výhodou způsobu podle vynálezu je, že je jednoduchý a látky se získávají v dobrých 230006 výtěžcích. Na delší syntézy barviv je možno vzít je bez čistění, jejich čistata je dostatečná. Pro Izolaci čistých produktů stačí je rozetřít v acetonu a vyvařit v methanolu.An advantage of the process of the invention is that it is simple and the substances are obtained in good 23,0006 yields. For longer synthesis of dyes they can be taken without purification, their purity is sufficient. To isolate pure products, just spread them in acetone and boil in methanol.
PřikladlHe did
2-Imino-3(gama-sulfopropyl)-5-chlorpyrldiniumbetain2-Imino-3 (gamma-sulfopropyl) -5-chloropyridinium betaine
Do tříhrdlé baňky o objemu 250 ml, opatřená míchadlem a zpětným chladičem, se vloží 2,5 g 2-amino-5-chlorpyridinu a 1,3 g 1,3-propansultonu. Směs se zahřívá za dobrého míchání při teplotě lázně 130 až 140 °C během 1,5 hodiny. Ke konci reakce je nutno míchání vypnout pro zatuhnutí produktu. Po ochlazení se směs reozetře v 50 ml acetonu a několikráte se promyje 30 ml acetonu. Po vysušení se dále čistí vyvařením v 50 ml methanolu. Po odsátí se suší pod infrelampou do konstantní hmotnosti. Výtěžek: 3,5 g (71,8 % teoretického výtěžku). Teplota tání: 328 až 329 °C.In a 250 ml three-necked flask equipped with a stirrer and reflux condenser was charged 2.5 g of 2-amino-5-chloropyridine and 1.3 g of 1,3-propanesultone. The mixture was heated with good stirring at a bath temperature of 130-140 ° C for 1.5 hours. At the end of the reaction, stirring should be turned off to solidify the product. After cooling, the mixture was re-metered in 50 ml of acetone and washed several times with 30 ml of acetone. After drying, it is further purified by boiling in 50 ml of methanol. After aspiration, it is dried under an infrared lamp to constant weight. Yield: 3.5 g (71.8% of theory). Melting point: 328-329 ° C.
Vzhled: bílé krystalky.Appearance: white crystals.
Elementární analýza:Elementary analysis:
Vypočteno: 038,32, H 4,42, N 11,17, S 12,78;H, 4.42; N, 11.17; S, 12.78.
Nalezeno: 038,26, H 4,33, N 11,29, S 12,85Found: 038.26, H 4.33, N 11.29, S 12.85
Přiklad 2Example 2
2-Imino-3(gama-sulfopropyl)pyridiniumbetain2-Imino-3 (gamma-sulfopropyl) pyridinium betaine
Do tříhrdlé kulaté baňky o objemu 250 ml, opatřené míchadlem a zpětným chladičem, se vloží 2,1 g 2-aminopyridinu a 1,3 g 1,3-propansultonu. Směs se zahřívá pe míchání při teplotě lázně 130 až 140 °C během 2 hodin. Ke konci reakce je nutno míchání vypnout pro zatuhnutí kvartérní soli. Po ochlazení se surový produkt rozetře v 50 ml acetonu a něolikráte promyje 30 ml acetonu. Po vysuěení se dále vyčistí vyvařením v 50 ml methanolu. Po odsátí se suší pod infralampou do konstantní hmotnosti. Výtěžek 3,6 g (74,6 % teoretického výtěžku). Teplota tání: 318 až 320 °C. Vzhled: bílé krystalky.In a 250 ml three-necked round-bottom flask equipped with a stirrer and reflux condenser was charged 2.1 g of 2-aminopyridine and 1.3 g of 1,3-propanesultone. The mixture was heated with stirring at a bath temperature of 130-140 ° C for 2 hours. At the end of the reaction, the stirring should be turned off to solidify the quaternary salt. After cooling, the crude product is triturated in 50 ml of acetone and washed several times with 30 ml of acetone. After drying, it is further purified by boiling in 50 ml of methanol. After aspiration, it is dried to a constant weight under infra-lamp. Yield 3.6 g (74.6% of theory). Melting point: 318-320 ° C. Appearance: white crystals.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS722179A CS225006B1 (en) | 1979-10-25 | 1979-10-25 | The preparation of intermediate products for the synthesis of asymmetrica 1 quinoline single azo cianine colouring agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS722179A CS225006B1 (en) | 1979-10-25 | 1979-10-25 | The preparation of intermediate products for the synthesis of asymmetrica 1 quinoline single azo cianine colouring agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS225006B1 true CS225006B1 (en) | 1984-02-13 |
Family
ID=5420971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS722179A CS225006B1 (en) | 1979-10-25 | 1979-10-25 | The preparation of intermediate products for the synthesis of asymmetrica 1 quinoline single azo cianine colouring agents |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS225006B1 (en) |
-
1979
- 1979-10-25 CS CS722179A patent/CS225006B1/en unknown
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