PL85142B1 - - Google Patents
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- Publication number
- PL85142B1 PL85142B1 PL1972158486A PL15848672A PL85142B1 PL 85142 B1 PL85142 B1 PL 85142B1 PL 1972158486 A PL1972158486 A PL 1972158486A PL 15848672 A PL15848672 A PL 15848672A PL 85142 B1 PL85142 B1 PL 85142B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- methoxy
- pyridine
- solvent
- reaction
- Prior art date
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- AHXDYBRGGOARRJ-UHFFFAOYSA-N 2-methoxy-5-methylsulfonylbenzamide Chemical compound COC1=CC=C(S(C)(=O)=O)C=C1C(N)=O AHXDYBRGGOARRJ-UHFFFAOYSA-N 0.000 claims 1
- -1 2-methoxy-5-methylsulfonylbenzyl Chemical group 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- QEFQGRZFYWPDSU-UHFFFAOYSA-N 2-methoxy-5-methylbenzoic acid Chemical compound COC1=CC=C(C)C=C1C(O)=O QEFQGRZFYWPDSU-UHFFFAOYSA-N 0.000 description 1
- SRJDBXFZGCCESY-UHFFFAOYSA-N C(C)N(CC)CCNP(=O)(N)N Chemical compound C(C)N(CC)CCNP(=O)(N)N SRJDBXFZGCCESY-UHFFFAOYSA-N 0.000 description 1
- JTVPZMFULRWINT-UHFFFAOYSA-N N-[2-(diethylamino)ethyl]-2-methoxy-5-methylsulfonylbenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(S(C)(=O)=O)=CC=C1OC JTVPZMFULRWINT-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/224—Phosphorus triamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarza¬ nia N-(dwuetyloaminoetylo)-2-metoksy-5-metylo- sulfonylobenzamidu o wzorze 3 i jego farmakolo¬ gicznie dopuszczalnych soli z kwasami nieorgani- czynymi i organicznymi oraz jego czwartorzedo¬ wych soli amoniowych, na drodze reakcji kwasu 2-metoksy-5-meitylosulfonylobenzoesowago o wzo- - rze 1, rozpuszczonego w rozpuszczalniku, zN,N',N/r- trlis- rze 2, wedlug schematu 1.Stosowany jako substcrat N,N',N"-tris-(dwuetylo- amdinoetylo)- fosforamiid o wrzoirze 2 otrzymuje sie sie na drodze reakcji tlenochlotrku fosforu z dwu- etyloaminoetyloamina wedlug schematu 2.Omówione znane reakcje prowadzi sie w obo¬ jetnych rozpuszczalnikach, przy czym najpierw wytraca sie zawsze ^hldrowodiorek fosforaniidu o wzorze 2, który oddziela sie i przeprowadza w zasade, a doipiero pózniej poddaje ja dalszej obróbce i reakcji z kwasem benzoesowym o wzo¬ rze 1.Kazdorazowe wyodrebnienie i oczyszczanie fo- sforoamidu o wzorze 2, stanowiacego oleista, le¬ pka substancje, trudna w obróbce, a zwlaszcza w oczyszczaniu, jest uciazliwe.Celem wynalazku jest wyeliminowanie omówio¬ nej niedogodnosci. W tym celu nalezy rozwiazac zagadnienie takiego prowadzenia sposobu, poprzez dobór odpowiedniego rozpuszczalnika, aby zbe¬ dnym stalo sie wyodrebnianie i Oczyszczanie f0- JO sforamidu przed wprowadzeniem go do reakcji "w sposobie wedlug wynalazku.Cel ten osiaga sie w sposobie wedlug wynalazku, polegajacym na tym, ze jako rozpuszczalnik w reakcji kwasu 2-metoksy-5-metylobenzoesowego o wzorze 1 z N,N',N,,-tris-l(dwuetyloaminoetylo)- -fosforamidem o wzorze 2 stosuje sie pirydyne.Stosowanie pirydyny równiez i w reakcji aminy z tlenochlorkiem fosforu (wedlug schematu 2) ma i]* zalete, ze pirydyna wiaze powstajacy kwas sol¬ ny a jednoczesnie rozpuszcza wolny, oleisty fosfo- ramid o wzorze 2, umozliwiajac tym samym dal¬ sza bezposrednia reakcje z kwasem benzoesowym o wzorze 1, wedlug schematu 1, w jednym ciagu i w jednym naczyniu reakcyjnym.Przy zastosowaniu pirydyny jako rozpuszcza¬ lnika jest wiec uprzednie wyodrebnianie i oczy¬ szczanie chlorowodorku fdsforamidu o wzorze 2 oraz jego przeksztalcanie w zasade zbedne. Dzieki zastosowaniu pirydyny jako rozpuszczalnika eli¬ minuje sie zatem co najmniej dwa zabiegi ope¬ racyjne, niezbedne w dotychczasowym, znanym sposobie postepowania, oraz unika sie uciazliwej manipulacji lepkim, oleistym fosforamidem.Sposób wedlug wynalazku ulatwia wiec i znacznie upraszcza otrzymywanie Nn(idjwiu€ityloaminoetylo)-2- metoksy-5-imetylos Podany nizej przyklad objasnia blizej sposób wedlug wynalazku. 85 14285 142 Przyklad. Otrzymywanie N-(dwuetyloamino- etyla)-2-metoksy-5-metyloisu;lfcinylobeinzaimidu.W naczyniu reakcyjnym o pojemnosci 1 litra rozpuszcza s:\% 36,5 g dwuetyloaminoetylc&immy w 840 ml pirydyny.Do roztworu w temperaturze otoczenia dodaje sie roztwór 6,1 g tlenochlorku fosforu w 65 ml pirydyny i miesza mieszanine reakcyjna w ciagu pól godziny.Nastepnie dodaje sie 22,1 g kwasu 2-meto1- kisy-5-metylosulfonylobenzcesowego, po czym mie¬ szanine reakcyjna ogrzewa sie w temperaturze wrzenia pod chlodni-a zwrotna w ciagu 4 godzin.Po zakonczeniu reakcji odparowuje sie pirydyne •rózni- i i 40 m! wody i 40 ml 36% kwasu solnego, w celu usunie¬ cia ewentualnych resztek nie przereagowanego kwasii. Roztwór, alkalizuje siie lugiem a otrzyma¬ lo ny osad odsacza sie i suszy. Otrzymuje sie 9 g N-(dwuetyloaminoeitylo)-2-metoiksy-5-metylosulfo- nylobenzamidu o temperaturze topnienia 120 — 122°C. -0=P(NH CHg-CHg-N^-H^), Schemat 2 Cena 10 zl PIZG KoszaMm D-4084. Naikl. 105 egz. PL PLThe present invention relates to a process for the preparation of N- (diethylaminoethyl) -2-methoxy-5-methylsulfonylbenzamide of the formula III and its pharmacologically acceptable salts with inorganic and organic acids and its quaternary ammonium salts by reaction 2-methoxy-5-meitylsulfonylbenzoic acid of formula 1, dissolved in solvent, with N, N ', N / r-triliser 2, according to scheme 1. Used as N, N', N "-tris- substituent (diethylamdinoethyl) phosphoramide boiling 2 is obtained by reacting phosphorus oxychloride with diethylaminoethylamine according to Scheme 2. which is separated and converted into the base, and then further processed and reacted with benzoic acid of the formula 1. It is difficult to process, and in particular to clean, difficult. The aim of the invention is to eliminate the disadvantage mentioned. To this end, it is necessary to solve the problem of such a method of carrying out the process by selecting a suitable solvent that it becomes necessary to isolate and purify the fO-JO sphoramide before introducing it into the reaction "in the method according to the invention. This aim is achieved in the method according to the invention, however, pyridine is used as a solvent in the reaction of 2-methoxy-5-methylbenzoic acid of the formula 1 with N, N ', N, - tris-1 (diethylaminoethyl) -phosphoramide of the formula 2. Pyridine is also used in the reaction of the amine. with phosphorus oxychloride (according to Scheme 2) has the advantage that pyridine binds the hydrochloric acid formed and at the same time dissolves the free, oily phosphoramidate of the formula II, thus allowing further direct reaction with the benzoic acid of the formula 1. according to Scheme 1, in one pass and in one reaction vessel. When pyridine is used as a solvent, there is therefore a prior isolation and purification of fdsforamide hydrochloride of the formula II and its cross section basically unnecessary. Due to the use of pyridine as a solvent, at least two procedures necessary in the current, known procedure are eliminated, and the cumbersome manipulation of viscous, oily phosphoramide is avoided. ) -2-methoxy-5-imethyls The following example explains the process according to the invention in more detail. 85 14 285 142 Ex. Preparation of N- (diethylaminoethyl) -2-methoxy-5-methylis; 1-cinylbeinzaimide. In a 1 liter reaction vessel, dissolve: \% 36.5 g of diethylaminoethylcum in 840 ml of pyridine. Add a solution of 6 to the solution at ambient temperature. 1 g of phosphorus oxychloride in 65 ml of pyridine and the reaction mixture is stirred for half an hour. Then 22.1 g of 2-methoxy-5-methylsulfonylbenzesic acid are added, and the reaction mixture is heated to reflux under cold conditions. and reflux within 4 hours. After the reaction is complete, the pyridine is evaporated off, • 40 m difference! of water and 40 ml of 36% hydrochloric acid to remove any unreacted acid residues. The solution is made alkaline with lye, and the obtained precipitate is filtered off and dried. 9 g of N- (diethylaminoeityl) -2-methoxy-5-methylsulfonylbenzamide with a melting point of 120-122 ° C are obtained. -0 = P (NH CHg-CHg-N ^ -H ^), Scheme 2 Price PLN 10 PIZG Basket mm D-4084. Naikl. 105 copies PL PL
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1080172A CH565145A5 (en) | 1972-07-19 | 1972-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL85142B1 true PL85142B1 (en) | 1976-04-30 |
Family
ID=4366997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972158486A PL85142B1 (en) | 1972-07-19 | 1972-10-26 |
Country Status (29)
| Country | Link |
|---|---|
| JP (1) | JPS5146105B2 (en) |
| KR (1) | KR780000255B1 (en) |
| AR (1) | AR194144A1 (en) |
| AT (1) | AT321284B (en) |
| AU (1) | AU466779B2 (en) |
| BE (1) | BE791677A (en) |
| BG (1) | BG19125A3 (en) |
| CA (1) | CA982147A (en) |
| CH (1) | CH565145A5 (en) |
| CS (1) | CS162785B2 (en) |
| DD (1) | DD100940A5 (en) |
| DE (1) | DE2256740C3 (en) |
| EG (1) | EG12820A (en) |
| ES (1) | ES407866A1 (en) |
| FR (1) | FR2192819B1 (en) |
| GB (1) | GB1364615A (en) |
| HU (1) | HU169293B (en) |
| IE (1) | IE36988B1 (en) |
| IL (1) | IL40840A (en) |
| LU (1) | LU66438A1 (en) |
| MC (1) | MC948A1 (en) |
| NL (1) | NL7214054A (en) |
| OA (1) | OA04218A (en) |
| PL (1) | PL85142B1 (en) |
| RO (1) | RO70188A (en) |
| SE (1) | SE402455B (en) |
| YU (1) | YU35874B (en) |
| ZA (1) | ZA728055B (en) |
| ZM (1) | ZM18372A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2206937B1 (en) * | 1972-11-22 | 1977-01-14 | Ile De France | |
| FR2305176A1 (en) * | 1975-03-28 | 1976-10-22 | Ile De France | NEW DRUG BASED ON N- (DIETHYLAMINOETHYL) 2-METHOXY-5-METHYL-SULFONYL BENZAMIDE |
| DE3148696A1 (en) * | 1981-12-09 | 1983-07-21 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING NITROARYLCARBONIC ACID NITROARYLAMIDES |
| FR2528702A1 (en) * | 1982-06-17 | 1983-12-23 | Ile De France | APPLICATION OF N- (DIETHYLAMINOETHYL) 2-METHOXY-5-METHYLSULFONYL BENZAMIDE IN THE INHIBITION OF TRYPTOPHAN PYRROLASE |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4940459B1 (en) * | 1970-12-21 | 1974-11-02 |
-
0
- BE BE791677D patent/BE791677A/en unknown
-
1972
- 1972-07-19 KR KR7201932A patent/KR780000255B1/en active
- 1972-07-19 CH CH1080172A patent/CH565145A5/xx not_active IP Right Cessation
- 1972-10-17 NL NL7214054A patent/NL7214054A/xx unknown
- 1972-10-17 SE SE7213359A patent/SE402455B/en unknown
- 1972-10-18 BG BG021657A patent/BG19125A3/en unknown
- 1972-10-23 ES ES407866A patent/ES407866A1/en not_active Expired
- 1972-10-23 CS CS7110A patent/CS162785B2/cs unknown
- 1972-10-26 PL PL1972158486A patent/PL85142B1/pl unknown
- 1972-10-27 HU HURE519A patent/HU169293B/hu unknown
- 1972-10-27 YU YU2680/72A patent/YU35874B/en unknown
- 1972-11-03 FR FR7239061A patent/FR2192819B1/fr not_active Expired
- 1972-11-07 CA CA155,846A patent/CA982147A/en not_active Expired
- 1972-11-09 LU LU66438A patent/LU66438A1/xx unknown
- 1972-11-10 MC MC1016A patent/MC948A1/en unknown
- 1972-11-10 GB GB5197272A patent/GB1364615A/en not_active Expired
- 1972-11-14 IL IL40840A patent/IL40840A/en unknown
- 1972-11-14 ZA ZA728055A patent/ZA728055B/en unknown
- 1972-11-16 AU AU48963/72A patent/AU466779B2/en not_active Expired
- 1972-11-18 OA OA54750A patent/OA04218A/en unknown
- 1972-11-18 DE DE2256740A patent/DE2256740C3/en not_active Expired
- 1972-11-22 AR AR245247A patent/AR194144A1/en active
- 1972-11-28 ZM ZM183/72*UA patent/ZM18372A1/en unknown
- 1972-12-05 IE IE1698/72A patent/IE36988B1/en unknown
- 1972-12-06 AT AT1038872A patent/AT321284B/en active
- 1972-12-26 JP JP734567A patent/JPS5146105B2/ja not_active Expired
- 1972-12-28 DD DD167950A patent/DD100940A5/xx unknown
-
1973
- 1973-02-09 RO RO7373793A patent/RO70188A/en unknown
- 1973-07-15 EG EG275/73A patent/EG12820A/en active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1364615A (en) | 1974-08-21 |
| ZA728055B (en) | 1973-07-25 |
| JPS4943945A (en) | 1974-04-25 |
| DE2256740A1 (en) | 1974-02-07 |
| NL7214054A (en) | 1974-01-22 |
| IL40840A0 (en) | 1973-01-30 |
| DE2256740C3 (en) | 1979-02-15 |
| AU4896372A (en) | 1974-05-16 |
| LU66438A1 (en) | 1973-02-01 |
| IE36988L (en) | 1974-01-19 |
| IL40840A (en) | 1975-12-31 |
| CS162785B2 (en) | 1975-07-15 |
| BE791677A (en) | 1973-03-16 |
| OA04218A (en) | 1979-12-31 |
| DD100940A5 (en) | 1973-10-12 |
| DE2256740B2 (en) | 1978-06-22 |
| ES407866A1 (en) | 1975-10-01 |
| RO70188A (en) | 1980-12-30 |
| JPS5146105B2 (en) | 1976-12-07 |
| EG12820A (en) | 1979-12-31 |
| KR780000255B1 (en) | 1978-07-06 |
| MC948A1 (en) | 1973-10-12 |
| AT321284B (en) | 1975-03-25 |
| FR2192819A1 (en) | 1974-02-15 |
| BG19125A3 (en) | 1975-04-30 |
| IE36988B1 (en) | 1977-04-13 |
| CA982147A (en) | 1976-01-20 |
| YU35874B (en) | 1981-08-31 |
| HU169293B (en) | 1976-10-28 |
| AR194144A1 (en) | 1973-06-22 |
| AU466779B2 (en) | 1975-11-06 |
| ZM18372A1 (en) | 1973-07-23 |
| FR2192819B1 (en) | 1975-10-31 |
| CH565145A5 (en) | 1975-08-15 |
| YU268072A (en) | 1981-02-28 |
| SE402455B (en) | 1978-07-03 |
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