DE2152370A1 - METHOD OF PRODUCING AN ANGULAR CLAMP ON (1-ETHYL-PYRROLIDINYL2) -METHYL ANGLE CLAMP TO -2-METHOXY5-SULFAMOYL-BENZAMIDE - Google Patents
METHOD OF PRODUCING AN ANGULAR CLAMP ON (1-ETHYL-PYRROLIDINYL2) -METHYL ANGLE CLAMP TO -2-METHOXY5-SULFAMOYL-BENZAMIDEInfo
- Publication number
- DE2152370A1 DE2152370A1 DE19712152370 DE2152370A DE2152370A1 DE 2152370 A1 DE2152370 A1 DE 2152370A1 DE 19712152370 DE19712152370 DE 19712152370 DE 2152370 A DE2152370 A DE 2152370A DE 2152370 A1 DE2152370 A1 DE 2152370A1
- Authority
- DE
- Germany
- Prior art keywords
- ethyl
- clamp
- sulfamoyl
- methyl
- benzamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 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 4
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 claims description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WMFCMIRCRKQLRO-UHFFFAOYSA-N 2-pyrrolidin-1-ylbutan-1-amine Chemical compound CCC(CN)N1CCCC1 WMFCMIRCRKQLRO-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux 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
- C07F9/547—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
-
- 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
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
FRATMANN A. G. CHENE-BOUGERIE/SchweizFRATMANN A. G. CHENE-BOUGERIE / Switzerland
Verfahren zur Herstellung von N - I (l-Aethyl-pyrrolidinyl-2)-methyl J -Z-methoxy-B-sulfamoyl-benzamidProcess for the preparation of N - I (1-ethyl-pyrrolidinyl-2) -methyl J -Z-methoxy-B-sulfamoyl-benzamide
Die Erfindung betrifft ein Verfahren zur Herstellung von N- l (1-Aethylpyrrolidinyl-2)-methyl I ^-methoxy-S-sulfamoyl-benzamid aus l-Aethyl-2-aminoinethyl-pyrrolidin und 2-Methoxy-5-sulfamoylbenzoesäure in einer sehr guten Ausbeute.The invention relates to a process for the preparation of N- l (1-ethylpyrrolidinyl-2) methyl I ^ -methoxy-S-sulfamoyl-benzamide from 1-ethyl-2-aminoethyl-pyrrolidine and 2-methoxy-5-sulfamoylbenzoic acid in a very good yield.
Dieses Verfahren ist erfindungsgemäss dadurch gekennzeichnet, dass 1-Aethyl-2-aminomethyl-pyrrolidin in Gegenwart von Phosphortrichlorid mit 2-Methoxy-5-sulfamoyl-benzoesäure umgesetzt wird.According to the invention, this method is characterized in that 1-ethyl-2-aminomethyl-pyrrolidine in the presence of phosphorus trichloride is reacted with 2-methoxy-5-sulfamoylbenzoic acid.
0900.F360.12D.2 - BIl/KW/es0900.F360.12D.2 - BIl / KW / es
309 8 08/1305309 8 08/1305
Als Reaktionsmedium kann hierbei vorzugsweise Pyridin verwendet werden.Pyridine can preferably be used here as the reaction medium will.
Die Umsetzungsreaktion verläuft hierbei nach folgendem Schema:The conversion reaction proceeds according to the following scheme:
NHNH
C2H5 C 2 H 5
+ PCI,+ PCI,
"Ν"Ν
C2H5 C 2 H 5
H N = P - NH - CHH N = P - NH - CH
C2H5 C 2 H 5
CH3OCH 3 O
COOHCOOH
I.I.
CONH-CH,CONH-CH,
C2H5 C 2 H 5
30 9 808/13030 9 808/130
-3- 215?370- 3 - 215? 370
In einen Kolben von 1 Liter Inhalt mit Rührer, Kühler, Thermometer und einem Tropfrichter bringt man 27 g (0,11 Mol) l-Aethyl-2-aminomethyl-pyrrolidin und 560 ml Pyridin. Man rührt die erhaltene Lösung und gibt tropfenweise 5,6 g (0,04 Mol) Phosphortrichlorid hinzu, gelöst in 64 ml Pyridin, wobei die Temperatur um 20 C gehalten wird.In a 1 liter flask with a stirrer, condenser, thermometer 27 g (0.11 mol) of 1-ethyl-2-aminomethyl-pyrrolidine are placed in a dropping funnel and 560 ml of pyridine. The solution obtained is stirred and 5.6 g (0.04 mol) of phosphorus trichloride are added dropwise added, dissolved in 64 ml of pyridine, the temperature being kept around 20 C.
Man ISsst noch eine halbe Stunde bei 20 C rühren und fügt dann 14,8 g (0,064 Mol) 2-Methoxy-5-sulfamoyl-benzoesäure hinzu. Man erhitzt dann viereinhalb Stunden unter Rückfluss und lässt die Reaktionsmischung über Nacht stehen. Dann wird das Pyridin im Vakuum abdestilliert und der Rückstand mit 200 ml 10%iger Salzsäure extrahiert. Man erhalt einen Niederschlag, welcher auf etwa 70 -80 C erhitzt wird und sich löst. Diese Lösung wird mit 15 ml konzentriertem Amoniak versetzt. Der hierbei gebildete Niederschlag wird abfiltriert, mit Wasser gewaschen und im Trockenschrank bei 50 C getrocknet.The mixture is stirred for a further half an hour at 20 ° C. and then 14.8 g are added (0.064 mol) 2-methoxy-5-sulfamoyl-benzoic acid was added. One heats up then reflux for four and a half hours and leaves the reaction mixture stand overnight. The pyridine is then distilled off in vacuo and the residue is extracted with 200 ml of 10% hydrochloric acid. A precipitate is obtained which has a temperature of about 70-80 ° C heats up and dissolves. This solution is concentrated with 15 ml Amonia added. The precipitate formed is filtered off, washed with water and dried in a drying cabinet at 50.degree.
Man erhält 16,2 g (=74,3% Ausbeute) an N- / (1-Aethyl-pyrrolidinyl-2)-methyl J -Z-methoxy-S-sulfamoyl-benzamid mit einem Schmelzpunkt von 178 C.16.2 g (= 74.3% yield) of N- / (1-ethyl-pyrrolidinyl-2) -methyl J -Z-methoxy-S-sulfamoyl-benzamide with a melting point of 178 ° C. are obtained.
Das N- [ (l-Aethyl-pyrrolidinyl-2)-methyl / ^-methoxy-S-sulfamoylbenzamid ist technisch verwendbar als wertvolles Zwischenprodukt in der pharmazeutischen Industrie, insbesondere zur Herstellung von Arzneimitteln zur Behandlung von Erkrankungen auf dem Gebiet der Gastro-Enterologie und Neurologie.The N- [(1-ethyl-pyrrolidinyl-2) -methyl / ^ -methoxy-S-sulfamoylbenzamide is technically usable as a valuable intermediate product in the pharmaceutical industry, in particular for the production of Medicines for the treatment of diseases in the field of gastro-enterology and neurology.
309808/ 1 305309808/1 305
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1226771A CH547797A (en) | 1971-08-20 | 1971-08-20 | PROCESS FOR THE PREPARATION OF N - ((1-AETHYL-PYRROLIDINYL2) -METHYL) -2-METHOXY-5-SULFAMOYL-BENZAMIDE. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2152370A1 true DE2152370A1 (en) | 1973-02-22 |
Family
ID=4381427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712152370 Pending DE2152370A1 (en) | 1971-08-20 | 1971-10-21 | METHOD OF PRODUCING AN ANGULAR CLAMP ON (1-ETHYL-PYRROLIDINYL2) -METHYL ANGLE CLAMP TO -2-METHOXY5-SULFAMOYL-BENZAMIDE |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS4829764A (en) |
| KR (1) | KR780000067B1 (en) |
| AT (1) | AT311328B (en) |
| BE (1) | BE774104A (en) |
| CA (1) | CA928714A (en) |
| CH (1) | CH547797A (en) |
| CS (1) | CS177818B2 (en) |
| DE (1) | DE2152370A1 (en) |
| DK (1) | DK126325B (en) |
| ES (1) | ES396718A1 (en) |
| FR (1) | FR2111372A5 (en) |
| GB (1) | GB1328747A (en) |
| HU (1) | HU166567B (en) |
| IE (1) | IE35821B1 (en) |
| IL (1) | IL38098A (en) |
| LU (1) | LU64275A1 (en) |
| MC (1) | MC897A1 (en) |
| NL (1) | NL7114902A (en) |
| NO (1) | NO136460C (en) |
| OA (1) | OA03928A (en) |
| PL (1) | PL84446B1 (en) |
| RO (1) | RO62479A (en) |
| SE (1) | SE376914B (en) |
| YU (1) | YU34286B (en) |
| ZA (1) | ZA717543B (en) |
| ZM (1) | ZM17771A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2252336B1 (en) * | 1973-11-27 | 1977-03-04 | Ile De France | |
| JPS5170235A (en) * | 1974-12-16 | 1976-06-17 | Toyo Aluminium Kk | |
| NZ186175A (en) * | 1977-01-27 | 1980-03-05 | Shionogi & Co | Meta-sulphonamidobenzamide derivatives |
| WO1991017144A1 (en) * | 1990-05-02 | 1991-11-14 | Yoshitomi Pharmaceutical Industries, Ltd. | Amide compound, pharmaceutical use thereof and novel 1-substituted pyrrolidinemethyl-amines |
-
1971
- 1971-08-20 CH CH1226771A patent/CH547797A/en not_active IP Right Cessation
- 1971-10-14 FR FR7136941A patent/FR2111372A5/fr not_active Expired
- 1971-10-18 BE BE774104A patent/BE774104A/en not_active IP Right Cessation
- 1971-10-21 DE DE19712152370 patent/DE2152370A1/en active Pending
- 1971-10-28 NL NL7114902A patent/NL7114902A/xx unknown
- 1971-11-05 ES ES396718A patent/ES396718A1/en not_active Expired
- 1971-11-08 CA CA127136A patent/CA928714A/en not_active Expired
- 1971-11-08 IL IL38098A patent/IL38098A/en unknown
- 1971-11-09 MC MC956A patent/MC897A1/en unknown
- 1971-11-09 SE SE7114275A patent/SE376914B/xx unknown
- 1971-11-09 YU YU2821/71A patent/YU34286B/en unknown
- 1971-11-09 ZA ZA717543A patent/ZA717543B/en unknown
- 1971-11-16 LU LU64275D patent/LU64275A1/xx unknown
- 1971-11-18 IE IE1459/71A patent/IE35821B1/en unknown
- 1971-11-29 DK DK584371AA patent/DK126325B/en not_active IP Right Cessation
- 1971-12-01 ZM ZM177/71*7A patent/ZM17771A1/xx unknown
- 1971-12-01 HU HUFA900A patent/HU166567B/hu unknown
- 1971-12-06 GB GB5649571A patent/GB1328747A/en not_active Expired
- 1971-12-06 KR KR7101750A patent/KR780000067B1/en active
- 1971-12-07 OA OA54434A patent/OA03928A/en unknown
- 1971-12-08 PL PL1971152013A patent/PL84446B1/pl unknown
- 1971-12-10 AT AT1064371A patent/AT311328B/en not_active IP Right Cessation
- 1971-12-29 CS CS9068A patent/CS177818B2/cs unknown
- 1971-12-29 JP JP47004153A patent/JPS4829764A/ja active Pending
- 1971-12-30 NO NO4949/71A patent/NO136460C/en unknown
-
1972
- 1972-01-15 RO RO7200069412A patent/RO62479A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZM17771A1 (en) | 1972-08-21 |
| LU64275A1 (en) | 1972-06-02 |
| BE774104A (en) | 1972-04-18 |
| ES396718A1 (en) | 1974-05-16 |
| CH547797A (en) | 1974-04-11 |
| SE376914B (en) | 1975-06-16 |
| CA928714A (en) | 1973-06-19 |
| RO62479A (en) | 1978-02-15 |
| FR2111372A5 (en) | 1972-06-02 |
| IE35821B1 (en) | 1976-05-26 |
| CS177818B2 (en) | 1977-08-31 |
| PL84446B1 (en) | 1976-04-30 |
| IL38098A (en) | 1974-12-31 |
| ZA717543B (en) | 1972-08-30 |
| MC897A1 (en) | 1972-06-22 |
| AT311328B (en) | 1973-11-12 |
| NO136460C (en) | 1977-09-07 |
| KR780000067B1 (en) | 1978-03-30 |
| NO136460B (en) | 1977-05-31 |
| YU282171A (en) | 1978-10-31 |
| YU34286B (en) | 1979-04-30 |
| GB1328747A (en) | 1973-08-30 |
| AU3572171A (en) | 1973-05-24 |
| IE35821L (en) | 1973-02-20 |
| IL38098A0 (en) | 1972-01-27 |
| NL7114902A (en) | 1973-02-22 |
| OA03928A (en) | 1975-08-14 |
| JPS4829764A (en) | 1973-04-19 |
| DK126325B (en) | 1973-07-02 |
| HU166567B (en) | 1975-04-28 |
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