CS276922B6 - 3-azidomethyl-4-hydroxyphenyl alkyl ketones and the preparation method - Google Patents
3-azidomethyl-4-hydroxyphenyl alkyl ketones and the preparation method Download PDFInfo
- Publication number
- CS276922B6 CS276922B6 CS6990A CS6990A CS276922B6 CS 276922 B6 CS276922 B6 CS 276922B6 CS 6990 A CS6990 A CS 6990A CS 6990 A CS6990 A CS 6990A CS 276922 B6 CS276922 B6 CS 276922B6
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- CS
- Czechoslovakia
- Prior art keywords
- azidomethyl
- preparation
- ketones
- formula
- alkyl ketones
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- -1 3-azidomethyl-4-hydroxyphenyl alkyl ketones Chemical class 0.000 title claims abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 16
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002576 ketones Chemical class 0.000 claims abstract description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 238000004458 analytical method Methods 0.000 claims description 2
- 238000002211 ultraviolet spectrum Methods 0.000 claims description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims 1
- 230000004071 biological effect Effects 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 150000003141 primary amines Chemical class 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- JEYCHXPRVCFCAQ-UHFFFAOYSA-N OC1=C(C=C(C=C1)CC(=O)CC1=CC(=C(C=C1)O)CCl)CCl Chemical compound OC1=C(C=C(C=C1)CC(=O)CC1=CC(=C(C=C1)O)CCl)CCl JEYCHXPRVCFCAQ-UHFFFAOYSA-N 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000013332 literature search Methods 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Riešenie sa týká nových 3-azidometyl- -4-hydroxyfenylalkylketónov všeobecného vzorca I, kde R je metyl a etyl. Spósob ich pripravy spočívá v tom, že na 4-hydroxy-3-chlórmetylfenylalkylketóny sa pósobí azidom sodným v dimetylformamide pri teplote 30 °C počas 24 hodin. Připravené nové 3-azidometyl-4-hydroxyfenvlalkylketóny všeobecného vzorca I móžu byt použité ako medziprodukty pre přípravu primárných amínov resp. solí, z ktorých je možné připravit nové látky s biologickou aktivitou.The solution concerns new 3-azidomethyl- 4-hydroxyphenylalkyl ketones of general interest of formula I wherein R is methyl and ethyl. The way they prepare is to do it The 4-hydroxy-3-chloromethylphenylalkyl ketones are with sodium azide in dimethylformamide 30 ° C for 24 hours. Ready new 3-azidomethyl-4-hydroxyphenyl alkyl ketones of the formula I can be used as intermediates for the preparation of primary amines respectively. salts from which to prepare new substances with biological activity.
Description
1 CS 276922 B6
Vynález sa týká nových 3-azidometyl-4-hydroxyfenylalkyl-ketónov všeobecného vzorca
kde R je metyl a etyl a spósobu ich přípravy.
Na základe literárnej rešerše ako i patentovej literatúrylátky uvedené pod všeobecným vzorcom I sú originálně doterazv literatúre nepopísané. Ide o deriváty p-hydroxyacetofenólua p-hydroxypropiofenólu, z ktorých mnohé vykazujú antibakteriál-nu, lokálnoanestetickú a antiarytmickú, beta-adrenolytickú akti-vitu. Připravené nové azidy všeobecného vzorca I móžu by£ použitéako medziprodukty pre přípravu primárných amínov resp. ich solí,z ktorých je možné připravit nové látky s biologickou aktivitu.
Spósob přípravy uvedených látok I spočívá v tom, že na4-hydroxy-3-chlórmetylfenylalkylketón připravený podlá SohdaS. a kol. J.Med.Chem. 22,279 /1979/ pósobí azidom sodným v dime-tylformamide pri teplote 30 °C. . Podrobnosti přípravy sú uvedené v nasledujúcom příklade. 3-az idomety1-4-hydroxyfenylmetylketón 0,lmol 4-hydroxy-3-chlórmetylfenylmetylketón sme rozpustili v 20ml bezvodého dimetylformamidu a po častiach sme přidali 0,1 molazidu sodného v 55 ml bezvodého dimetylformamidu tak, aby teplotareakčnej zmesi neprestúpila 30 °C. Potom sa reakčná zmes miešala24 hodin pri teplote miestnosti. Vylúčený chlorid sodný sa odfil-troval a dimetyiformamid sa volné odpařil na hodinových sklíč-kách. Získaná biela kryštalická látka sa přečistila kryštalizáci-ou z etylacetátu. Výtažok 60 %. Teplota topenia 140 až 143 °C/nekorigovaná/
Analýza pre CqH9N3O2 /Mr. = 191,18 /vypočítaná % C =56,54.,% H = 4,74., % N = 21,97., zistené % C = 56,24., % H = 4,85.,% N = 21,72.
Infračeprené spektrum /nujol/V /C=C/ 1584 cm”1., /0=0/1666 cm“1.,V /N-,/ = 2088 /dva alebo rozlišené pásy/., y /OH/ =3 200 - 3 500 cm T.
Ultrafialové spektrum /metanol/ λmax = 228 nm /log^* = 3,71/272 nm /logf = 3,73/.
1H-NMR
ch2-N
1 CS 276922 B6
The present invention relates to novel 3-azidomethyl-4-hydroxyphenylalkyl ketones of the general formula
wherein R is methyl and ethyl and a method for their preparation.
Based on the literature search as well as the patent literature, the compounds of formula (I) have not been previously described in the literature. These are p-hydroxyacetophenol and p-hydroxypropiophenol derivatives, many of which exhibit antibacterial, local anesthetic and antiarrhythmic, beta-adrenolytic activity. The prepared novel azides of the formula I can be used as intermediates for the preparation of primary amines, respectively. salts thereof, from which new substances with biological activity can be prepared.
The method of preparing said compounds I is that the 4-hydroxy-3-chloromethylphenylalkyl ketone prepared according to SohdaS. et al. J.Med.Chem. 22,279 (1979) with sodium azide in dimethylformamide at 30 ° C. . Details of the preparation are given in the following example. 3-azomethyl-4-hydroxyphenylmethyl ketone 0.1mol 4-Hydroxy-3-chloromethylphenylmethylketone was dissolved in 20mL of anhydrous dimethylformamide and 0.1mol of sodium sodium molazide in 55mL of anhydrous dimethylformamide was added portionwise to avoid a temperature of 30 ° C. Then the reaction mixture was stirred at room temperature for 24 hours. The precipitated sodium chloride was filtered off and the dimethyiformamide was freely evaporated on an hour slide. The white crystalline solid obtained was purified by crystallization from ethyl acetate. Yield 60%. Mp 140-143 ° C (uncorrected)
Analysis for C 10 H 9 N 3 O 2 / Mr. = 191.18 (calculated% C = 56.54,% H = 4.74,% N = 21.97, found% C = 56.24,% H = 4.85,% N = 21.72.
Infrared Spectrum / Nujol / V / C = C / 1584 cm 1, 1/0 = 0/1666 cm 1, V / N -, / = 2088 / two or differentiated bands / y, OH / = 3 200-3,500 cm T.
Ultraviolet Spectrum / Methanol (λ max = 228 nm / log log = 3.71 / 272 nm (logf = 3.73).
1 H-NMR
ch2-N
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS6990A CS276922B6 (en) | 1990-01-05 | 1990-01-05 | 3-azidomethyl-4-hydroxyphenyl alkyl ketones and the preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS6990A CS276922B6 (en) | 1990-01-05 | 1990-01-05 | 3-azidomethyl-4-hydroxyphenyl alkyl ketones and the preparation method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS9000069A2 CS9000069A2 (en) | 1991-07-16 |
| CS276922B6 true CS276922B6 (en) | 1992-09-16 |
Family
ID=5332208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS6990A CS276922B6 (en) | 1990-01-05 | 1990-01-05 | 3-azidomethyl-4-hydroxyphenyl alkyl ketones and the preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS276922B6 (en) |
-
1990
- 1990-01-05 CS CS6990A patent/CS276922B6/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS9000069A2 (en) | 1991-07-16 |
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