NO140347B - Fremgangsmaate ifoelge norsk patent 136.460 ved fremstilling av n-(1-ethyl-alfa-pyrrolidyl-methyl)-2-methoxy-5-sulfamidobenzamid - Google Patents
Fremgangsmaate ifoelge norsk patent 136.460 ved fremstilling av n-(1-ethyl-alfa-pyrrolidyl-methyl)-2-methoxy-5-sulfamidobenzamid Download PDFInfo
- Publication number
- NO140347B NO140347B NO3232/72A NO323272A NO140347B NO 140347 B NO140347 B NO 140347B NO 3232/72 A NO3232/72 A NO 3232/72A NO 323272 A NO323272 A NO 323272A NO 140347 B NO140347 B NO 140347B
- Authority
- NO
- Norway
- Prior art keywords
- formula
- ethyl
- methoxy
- pyridine
- procedures according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- SQAILWDRVDGLGY-UHFFFAOYSA-N 2-methoxy-5-sulfamoylbenzoic acid Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(O)=O SQAILWDRVDGLGY-UHFFFAOYSA-N 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 2
- WMFCMIRCRKQLRO-UHFFFAOYSA-N 2-pyrrolidin-1-ylbutan-1-amine Chemical compound CCC(CN)N1CCCC1 WMFCMIRCRKQLRO-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000028774 intestinal disease Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 208000018556 stomach disease Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Electrical Discharge Machining, Electrochemical Machining, And Combined Machining (AREA)
- Superconductors And Manufacturing Methods Therefor (AREA)
Description
Foreliggende oppfinnelse er en videre utvikling av fremgangsmåten ifølge norsk patent 136.460 og angår en enkel og for-delaktig fremgangsmåte ved fremstilling av N-(1-ethyl-a-pyrroli-dylmethyl)-2-methoxy-5-sulfamidobenzamid, hvilket kan anvendes ved behandling av mave- og tarmsykdommer, såvel som innen psykia-trien.
Nærmere bestemt angår oppfinnelsen en fremgangsmåte ifølge norsk patent 136.460 ved fremstilling av N-[(1-ethylpyrro-lidinyl-2-)-methyl]-2-methoxy-5-sulfamoylbenzamid av formelen: ^VS°2NH2
CH3°SC^O-J NH-CH, -k I s1(I)
2 >r
i
<C>2<H>5
ved hvilken fremgangsmåte l-ethyl-2-aminomethylpyrrolidin av formelen:
H„N-CH_—k. J f11)
<i>2<H>5
omsettes i pyridin med fosfortriklorid, hvorefter mellomproduktet uten isolering omsettes i pyridin med 2-methoxy-5-sulfamoyl-benzoesyre av formelen:
under dannelse av benzamidet av formel (I), hvilken fremgamgsmåte er kjennetegnet ved at der som fosforforbindelse anvendes 1 mol fosforoxyklorid pr. 3 mol l-ethyl-2-aminomethylpyrrolidin.
Fremgangsmåten forløper efter følgende reaksjohsskjerna:
Den nye fremgangsmåte kan på en enkel måte gjennomfø-res praktisk slik det etterfølgende eksempel beskriver.
Et reaksjonskar på 1 liter ble utstyrt med en rører, termometer og kjøler, såvel som en dråpetrakt. I denne reak-sjonskolbe ble innført 27 g (0,21 mol) N-ethyl-o-aminomethyl-pyrrolidin og 560 ml pyridin.
I denne oppløsning ble dråpevis tilsatt ved en tempera-tur av 20°C en oppløsning av 6,1 g (0,04 mol) fosforoxyklorid i 65 ml pyridin. Innholdet ble omrørt en halv time, hvorefter 14,8 g (0,064 mol) 2-methoxy-5-sulfamidobenzoesyre ble tilført, og blandingen ble kokt 4 1/2 time ved tilbakeløpskjøling.
Den erholdte reaksjonsblanding ble under redusert trykk inndampet til det halve volum, filtrert, og filtratet ble inndampet til tørrhet. Det gjenværende produkt ble oppløst i 200 ml vann og ved tilsetning av 40 ml saltsyre bragt til en pH på 1.
Den filtrerte oppløsning fikk stå over natten i et kjø-leskap, ble derefter filtrert, og bunnfallet ble tørket i varmeskap ved 50°C.
Dette bunnfall ble oppløst i varmt vann. En mindre opp-løselig rest ble filtrert under kokning, hvorefter den varme opp-løsning ble gjort alkalisk med ammoniakk.
Oppløsningen ble avkjølt, filtrert, vasket med vann, og bunnfallet ble tørket i varmeskap ved 50°C. Der ble erholdt 7,5 g N-(1-ethyl-a-pyrrolidylmethyl)-2-methoxy-5-sulfamidobenzamid med smeltepunkt 179°C.
Analyse av nitrogeninnholdet ved hjelp av perklorsyre (100 %) ga en nitrogenverdi på 12,4 g (beregnet 12,32 %).
Mellomproduktet N,N'N"-(1-ethyl-a-pyrrolidylmethyl)-fosforamid kan isoleres i form av en hygroskopisk blanding fra di-og triklorhydratet når omsetningen av N-ethyl-a-aminomethyl-pyrro-lidin med fosforoxyklorid utføres i dioxan som oppløsningsmiddel og reaksjonsmedium.
Claims (1)
- Fremgangsmåte ifølge patent nr. 136.460 ved fremstilling " av N-t(l-ethylpyrrolidinyl-2-)-methyl]-2-methoxy-5-sulfamoyl-benzamid av formelen:ved hvilken fremgangsmåte l-ethyl-2-aminomethylpyrrolidin av formelen:omsettes i pyridin med fosfortriklorid, hvorefter mellomproduktet uten isolering omsettes i pyridin med 2-methoxy-5-sulfamoyl-benzoe-syre av formelen:under dannelse av benzamidet av formel (I), karakterisert ved at der som fosforforbindelse anvendes 1 mol fosforoxyklorid pr. 3 mol l-ethyl-2-aminoethylpyrrolidin.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH881372A CH562790A5 (no) | 1972-06-13 | 1972-06-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO140347B true NO140347B (no) | 1979-05-07 |
| NO140347C NO140347C (no) | 1979-08-15 |
Family
ID=4345021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3232/72A NO140347C (no) | 1972-06-13 | 1972-09-12 | Fremgangsmaate ifoelge norsk patent 136.460 ved fremstilling av n-(1-ethyl-alfa-pyrrolidyl-methyl)-2-methoxy-5-sulfamidobenzamid |
Country Status (31)
| Country | Link |
|---|---|
| JP (1) | JPS565733B2 (no) |
| AR (1) | AR193288A1 (no) |
| AT (1) | AT316536B (no) |
| AU (1) | AU464143B2 (no) |
| BE (1) | BE787180A (no) |
| BG (1) | BG20575A3 (no) |
| CA (1) | CA976554A (no) |
| CH (1) | CH562790A5 (no) |
| CS (1) | CS181712B2 (no) |
| DD (1) | DD100249A5 (no) |
| DE (1) | DE2246799A1 (no) |
| EG (1) | EG10796A (no) |
| ES (1) | ES407141A1 (no) |
| FI (1) | FI59243C (no) |
| FR (1) | FR2187782B1 (no) |
| GB (1) | GB1345494A (no) |
| HU (1) | HU165916B (no) |
| IE (1) | IE36719B1 (no) |
| IL (1) | IL40503A (no) |
| IT (1) | IT1034031B (no) |
| LU (1) | LU65860A1 (no) |
| MC (1) | MC938A1 (no) |
| NL (1) | NL7213128A (no) |
| NO (1) | NO140347C (no) |
| OA (1) | OA04167A (no) |
| PL (1) | PL83580B1 (no) |
| RO (1) | RO60562A (no) |
| SE (1) | SE385695B (no) |
| YU (1) | YU35119B (no) |
| ZA (1) | ZA726084B (no) |
| ZM (1) | ZM15172A1 (no) |
-
0
- BE BE787180D patent/BE787180A/xx not_active IP Right Cessation
-
1971
- 1971-08-24 AR AR243725A patent/AR193288A1/es active
-
1972
- 1972-06-13 CH CH881372A patent/CH562790A5/xx not_active IP Right Cessation
- 1972-08-07 LU LU65860A patent/LU65860A1/xx unknown
- 1972-08-22 MC MC1007A patent/MC938A1/xx unknown
- 1972-08-30 IT IT28620/72A patent/IT1034031B/it active
- 1972-08-31 FR FR7230990A patent/FR2187782B1/fr not_active Expired
- 1972-09-02 OA OA54681A patent/OA04167A/xx unknown
- 1972-09-04 GB GB4087072A patent/GB1345494A/en not_active Expired
- 1972-09-06 ZA ZA726084A patent/ZA726084B/xx unknown
- 1972-09-07 AU AU46416/72A patent/AU464143B2/en not_active Expired
- 1972-09-12 NO NO3232/72A patent/NO140347C/no unknown
- 1972-09-12 SE SE7211723A patent/SE385695B/xx unknown
- 1972-09-14 CA CA151,723A patent/CA976554A/en not_active Expired
- 1972-09-15 FI FI2549/72A patent/FI59243C/fi active
- 1972-09-15 CS CS7200006345A patent/CS181712B2/cs unknown
- 1972-09-18 HU HUEA921A patent/HU165916B/hu unknown
- 1972-09-19 IE IE1280/72A patent/IE36719B1/xx unknown
- 1972-09-19 ZM ZM151/72*UA patent/ZM15172A1/xx unknown
- 1972-09-20 PL PL1972157841A patent/PL83580B1/pl unknown
- 1972-09-21 AT AT812672A patent/AT316536B/de not_active IP Right Cessation
- 1972-09-23 DE DE19722246799 patent/DE2246799A1/de active Pending
- 1972-09-25 YU YU2421/72A patent/YU35119B/xx unknown
- 1972-09-28 NL NL7213128A patent/NL7213128A/xx unknown
- 1972-09-29 ES ES407141A patent/ES407141A1/es not_active Expired
- 1972-09-29 DD DD165950A patent/DD100249A5/xx unknown
- 1972-09-30 RO RO72382A patent/RO60562A/ro unknown
- 1972-10-04 IL IL40503A patent/IL40503A/xx unknown
- 1972-10-12 BG BG021603A patent/BG20575A3/xx unknown
- 1972-12-28 EG EG547/72A patent/EG10796A/xx active
-
1973
- 1973-02-01 JP JP1332573A patent/JPS565733B2/ja not_active Expired
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