NO130312B - - Google Patents
Download PDFInfo
- Publication number
- NO130312B NO130312B NO02049/71*[A NO204971A NO130312B NO 130312 B NO130312 B NO 130312B NO 204971 A NO204971 A NO 204971A NO 130312 B NO130312 B NO 130312B
- Authority
- NO
- Norway
- Prior art keywords
- formula
- formaldehyde
- benzyl
- compound
- hydrogen atom
- Prior art date
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- ULZRKSDAMUWQEZ-UHFFFAOYSA-N 1-anilinoethanol Chemical class CC(O)NC1=CC=CC=C1 ULZRKSDAMUWQEZ-UHFFFAOYSA-N 0.000 claims description 7
- -1 alkali metal borate Chemical class 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910021538 borax Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000010339 sodium tetraborate Nutrition 0.000 description 3
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000007031 hydroxymethylation reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
- C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
- C07C215/60—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain the chain having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Fremgangsmåte for fremstilling av
fenylaminoetanolderivater.
Denne oppfinnelse angår en fremgangsmåte for fremstilling
av visse fenylaminoetanolderivater.
Vi har funnet at fenylaminoetanolderivater med den nedenstående formel I kan fremstilles fra forbindelser med den nedenstående formel II ved behandling med-formaldehyd i nærvær av en sterk base og et alkalimetallborat.
I henhold til oppfinnelsen tilveiebringes således en fremgangsmåte for fremstilling av fenylaminoetanolderivater med formel I:
hvor betyr et hydrogenatom eller en benzy.lgruppe, bg 1*2 betyr et hydrogenatom eller en lineær eller forgrenet alkylgruppe inneholdende fra 1 til 6 karbonatomer eller en aryl-alkylgruppe. Fremgangsmåten karakteriseres ved at en forbindelse med formel II: ;hvor R-, og R ? har de ovenfor angitte betydninger, behandles med formaldehyd eller en formaldehydavgivende forbindelse i nærvær av en sterk base og et alkalimetallborat, hvorefter man, om ønsket, debenzylerer et erholdt fenylaminoetanolderivat, i hvilket R<1> er en benzylgruppe. ;Nærvær av et alkalimetallborat fører uventet til selektiv monohydroksymetylering i 3-stilling i stedet for hydroksymetylering i både 3- og 5-stilling. ;Ved utførelse av omsetningen kan man anvende formaldehyd ;selv eller enhver egnet kilde for formaldehyd så som paraformaldehyd. En vandig oppløsning av formaldehyd, f.eks. 40 % formalin foretrekkes. Omsetningen utføres i nærvær av en sterk base, fortrinnsvis et alkali-metallhydroksyd så som natriumhydroksyd, og et alkalimetallborat, særlig natriumborat. Omsetningen utføres fortrinnsvis ved omgivelses-temperatur i vandig oppløsning. ;Forbindelsene med formel I er beskrevet i vårt norske patent 126.014 som mellomprodukter ved fremstilling av fenylaminoetanoler med formel III som er 8-adrenerge stimulerende midler og nyttige som bronkodilatorer. ;Den katalytiske hydrogenolyse av forbindelser med formel (I) ;(Rj, benzyl,R2 tert.butyl eller benzyl) for å danne forbindelser med formel (III) (R^ = tert.butyl eller H) og den reduk-tive alkylering av sistnevnte med aldehyder eller ketoner til pro-dukter med formel (III) hvor R^ kan ha en rekke, forskjellige betydninger, f.eks. p-metoksy~a-metylfenetyl er beskrevet i nevnte patent. ;Fremgangsmåten i henhold til oppfinnelsen har den fordel sammenlignet med de kjente fremgangsmåter for fremstilling av disse forbindelser (se eksempel 8 i norsk patent 126.014) at innføringen av hydroksymetylgruppen finner sted i et enkelt trinn. ;Eksempel 1 ;1 13 a - ( benzyl- tert- butylaminometyl)- 4- hydroksy- m- xylen- g , a - diol ;a- (benzyl-tert-butylaminometyl)-4-hydroksy-benzylalkohol-hydroklorid (1,0 g) ble satt til en oppløsning av natriumhydroksyd (0,24 g) i vann (50 ml) og dioksan (20 ml), og blandingen ble om-rørt inntil man fikk en klar oppløsning. En oppløsning av natriumborat (2,3 g) i vann (50 ml) og 36 % formaldehyd (5 ml) ble tilsatt, og oppløsningen ble holdt ved romtemperatur inntil alt utgangsmateriale hadde reagert (7-25 dager). Reaksjonsblandingen ble surgjort ved tilsetning av 2N saltsyre og ble deretter gjort basisk med et overskudd av 8 % natriumbikarbonat. Produktet ble ekstrahert inn i etylacetat, vasket med saltoppløsning og tørret (Na2S0^). Konsen-trering ga en klar olje som krystalliserte langsomt. Omkrystalli-sering fra~ etylacetat-petroleter (k.p. 60-80°c) ga a -benzyl-tert-butylaminometyl-4-hydroksy-m-xylen-a 1 , a 3-diol (0,35 g; 35 %) sm.p. 118-119°c. Smeltepunktet ble ikke senket ved blanding med en autentisk prøve isolert fra fremgangsmåten beskrevet i eksempel 8 i norsk patent 126.014. Eksempel 2 ;a ^-- ( dibenzylaminometyl) - 4- hydroksy- m- xylen- g"*", q^- diol
Natriumhydroksyd (lN) (2 ml) og dioksan (15 ml) ble satt til en suspensjon av a -(dibenzylaminometyl)-4-hydroksybenzyl-alkohol (0,666 g) i vann (15 ml), og blandingen ble omrørt inntil man fikk en klar oppløsning. En oppløsning av natriumborat (0,76 g) i vann (10 ml) og 36 % formaldehyd (5 ml) ble tilsatt, og oppløsningen ble holdt ved romtemperatur inntil alt utgangsmateriale hadde reagert
(7-25 dager). Reaksjonsblandingen ble surgjort ved tilsetning av 2N saltsyre og ble deretter gjort basisk med overskudd åv 8 % natriumbikarbonat. Etter fortynning med et likt volum vann ble det hvite bunnfall frafiltrert og lufttørret. Det faste materiale ble
oppløst i etylacetat, filtrert gjennom en kort kolonne av kisel-syre, og filtratet og vaskevæskene ble samlet; og tørret (Na2S0^) . Konsentrering av oppløsningen ga et hvitt, fast stoff som ble krystallisert fra etylacetat-cykloheksan' for å gi a^-dibenzylaminometyl-4-hydroksy-m-xylen-a! 1 , a 3-diol (0,3 g) sm.p. 108-110°C. Smeltepunktet ble ikke senket ved. blanding med en autentisk prøve, fremstilt i henhold til eksempel 22 i norsk patent 126.014. Denne kan deretter debenzyleres ved fremgangsmåten beskrevet i eksempel 12 i nevnte norske patent for å gi a^-aminometyl-4-hydroksy-m-xylen-a 1 , a 3-diol (R.j=R2=H) . Denne forbindelse kan deretter alkyleres reduktivt ved fremgangsmåten beskrevet i eksemplene 17, 18, 19, 20 og 21 i nevnte norske patent.
Claims (1)
- Fremgangsmåte for fremstilling av fenylaminoetanolderivater med formel I:hvor R-^ betyr et hydrogenatom eller en benzylgruppe, og R2 betyr et hydrogenatom eller en lineær eller forgrenet alkylgruppe inneholdende fra 1 til 6 karbonatomer eller en aralkyl-gruppe, karakterisert ved at en forbindelse med formel II: hvor R^ og R har de ovenfor angitte betydninger, omsettes med formaldehyd eller en formaldehydavgivende forbindelse i nærvær av en sterk base og et alkalimetallborat, hvoretter man, om ønsket, debenzylerer en erholdt forbindelse med formel I hvor R^ er benzyl.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26523/70A GB1298284A (en) | 1970-06-02 | 1970-06-02 | Preparation of phenylaminoethanols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO130312B true NO130312B (no) | 1974-08-12 |
Family
ID=10244972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO02049/71*[A NO130312B (no) | 1970-06-02 | 1971-06-01 |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5216102B1 (no) |
| AT (1) | AT308724B (no) |
| CA (1) | CA989418A (no) |
| CH (1) | CH558329A (no) |
| DE (1) | DE2127177C3 (no) |
| DK (1) | DK125388B (no) |
| ES (1) | ES391800A1 (no) |
| FI (1) | FI56823C (no) |
| GB (1) | GB1298284A (no) |
| IL (1) | IL36836A (no) |
| NL (1) | NL174040C (no) |
| NO (1) | NO130312B (no) |
| SE (1) | SE376764B (no) |
| YU (1) | YU34979B (no) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51118737A (en) * | 1975-04-10 | 1976-10-18 | Shionogi & Co Ltd | Novel process for preparation of monosubstituted aminobenzylalcohols a t o-n position |
| EP0259159A3 (en) * | 1986-09-05 | 1989-08-09 | Schering Corporation | Method for the preparation of alpha1- [[(1,1-Dimethylethyl) amino] methyl]-4-hydroxy-1,3-benzenedimethanol, and intermediates used in its preparation |
| US4952729A (en) * | 1986-09-05 | 1990-08-28 | Schering-Plough Corp. | Intermediates in the preparation of alpha1(((1,1-dimethylethyl) amino) methyl)-4-hydroxy-1,3-benzenedimethanol |
-
1970
- 1970-06-02 GB GB26523/70A patent/GB1298284A/en not_active Expired
-
1971
- 1971-05-11 CA CA112,656A patent/CA989418A/en not_active Expired
- 1971-05-12 IL IL36836A patent/IL36836A/en unknown
- 1971-05-20 YU YU1271/71A patent/YU34979B/xx unknown
- 1971-05-21 FI FI1389/71A patent/FI56823C/fi active
- 1971-05-26 JP JP46035603A patent/JPS5216102B1/ja active Pending
- 1971-05-28 AT AT464071A patent/AT308724B/de not_active IP Right Cessation
- 1971-05-31 ES ES391800A patent/ES391800A1/es not_active Expired
- 1971-06-01 DK DK264671AA patent/DK125388B/da unknown
- 1971-06-01 DE DE2127177A patent/DE2127177C3/de not_active Expired
- 1971-06-01 NO NO02049/71*[A patent/NO130312B/no unknown
- 1971-06-02 SE SE7107128A patent/SE376764B/xx unknown
- 1971-06-02 CH CH798871A patent/CH558329A/xx not_active IP Right Cessation
- 1971-06-02 NL NLAANVRAGE7107588,A patent/NL174040C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| YU34979B (en) | 1980-06-30 |
| FI56823B (fi) | 1979-12-31 |
| SE376764B (no) | 1975-06-09 |
| NL7107588A (no) | 1971-12-06 |
| IL36836A0 (en) | 1971-07-28 |
| DE2127177C3 (de) | 1981-01-29 |
| CH558329A (de) | 1975-01-31 |
| GB1298284A (en) | 1972-11-29 |
| AT308724B (de) | 1973-07-25 |
| NL174040B (nl) | 1983-11-16 |
| ES391800A1 (es) | 1974-11-01 |
| YU127171A (en) | 1979-12-31 |
| NL174040C (nl) | 1984-04-16 |
| IL36836A (en) | 1973-07-30 |
| CA989418A (en) | 1976-05-18 |
| DE2127177A1 (de) | 1971-12-09 |
| JPS5216102B1 (no) | 1977-05-06 |
| DK125388B (da) | 1973-02-12 |
| FI56823C (fi) | 1980-04-10 |
| DE2127177B2 (de) | 1980-05-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO136947B (no) | Bredb}ndsrundstr}leantenne. | |
| US4996327A (en) | Preparation of pyrazole and its derivatives | |
| Begtrup et al. | Reactions of glyoxals with hydrazones: a new route to 4-hydroxypyrazoles | |
| NO130312B (no) | ||
| USRE28242E (en) | Method for manufacturing tetronic acid | |
| CZ286450B6 (en) | Process for preparing o-aminophenylcyclopropyl ketone | |
| US2695290A (en) | Derivatives of indole and method for the production thereof | |
| US3824255A (en) | Process for the production of tetronic acid | |
| SU492076A3 (ru) | Способ получени замещенных гуанидина | |
| JP2578797B2 (ja) | Ｎ−（スルホニルメチル）ホルムアミド類の製造法 | |
| US3867455A (en) | Preparation of phenylaminoethanols | |
| NO137093B (no) | Fremgangsm}te til fremstilling av 2,4-diamino-5-benzylpyrimidiner | |
| US1866956A (en) | Phenyl-indol-sulphonic acids | |
| SU650504A3 (ru) | Способ получени метил-(2-хиноксалинилметилен)-карбазат-диоксида | |
| Marion et al. | The Synthesis of l-Roemerine1 | |
| NO130218B (no) | ||
| US3956301A (en) | Process for bromination of pyrimidine | |
| SU426366A3 (ru) | Способ получения производных1-арил-2,3,4,5 тетрагидро-1 н-1,5-бензодиазепин-2-она | |
| US2895965A (en) | Process for the production of | |
| US2812323A (en) | Des-n-methyl erythromycin | |
| US3758515A (en) | Method for manufacturing tetronic acid | |
| NO163557B (no) | Kassettfilter. | |
| SU117044A1 (ru) | Способ получени 1-фенил-2, 3 диметил-4-диметиламинопиразолона-5 (пирамидона) | |
| SU533584A1 (ru) | Способ получени 4-бром-2,3,5,6тетраметилфенола | |
| SU384331A1 (ru) | Способ получени 1-замещенных карбамоил-4(2-оксиарил)-семинарбазидов |