MC897A1 - Process for the preparation of N-Ú (ethyl-1-pyrrolidinyl-2) methyl¾ methoxy-2-sulfamoyl-5-benzamide - Google Patents
Process for the preparation of N-Ú (ethyl-1-pyrrolidinyl-2) methyl¾ methoxy-2-sulfamoyl-5-benzamideInfo
- Publication number
- MC897A1 MC897A1 MC956A MC956A MC897A1 MC 897 A1 MC897 A1 MC 897A1 MC 956 A MC956 A MC 956A MC 956 A MC956 A MC 956A MC 897 A1 MC897 A1 MC 897A1
- Authority
- MC
- Monaco
- Prior art keywords
- methoxy
- ethyl
- sulfamoyl
- pyrrolidinyl
- benzamide
- Prior art date
Links
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)
- Pyrrole Compounds (AREA)
Description
BREVET D'INVENTION PATENT FOR INVENTION
.Procède de préparation du N- jjéthyl-l-pyrrolidinyl-2)- méthylj -méthoxy- 2-sulfamoyl-5-benzamide Process for preparing N-ethyl-1-pyrrolidinyl-2-methyl-2-methoxy-sulfamoyl-5-benzamide
FRATMANN S.A. FRATMANN S.A.
La présente invention concerne un procédé de préparation du N-£ (éthyl-l-pyrrolidinyl- 2) -méthyl J -méthoxy-2-sulfamoyl-5-benzamide à partir d'acide méthoxy-2-sulfamoyl-5-benzoi"que et d'éthyl-1-aminométhyl-2-pyrrolidinë permettant d'obtenir un très bon rendement. The present invention relates to a process for preparing N-Σ (ethyl-1-pyrrolidinyl-2)-methyl α-methoxy-2-sulfamoyl-5-benzamide from methoxy-2-sulfamoyl-5-benzoic acid and ethyl-1-aminomethyl-2-pyrrolidin, allowing for a very good yield.
Le procédé selon l'invention est caractérisé essentiellement en ce que l'on fait réagir l'acide méthoxy-2-sulfamoyl-5-benzoi'que et l'éthyl-1-aminométhyl-2-pyrrolidine en présence de trichlorure de phosphore. The process according to the invention is characterized essentially in that methoxy-2-sulfamoyl-5-benzoic acid and ethyl-1-aminomethyl-2-pyrrolidine are reacted in the presence of phosphorus trichloride.
Comme milieu de réaction on utilise de préférence la pyridine. Pyridine is preferably used as the reaction medium.
La réaction-se produit selon le schéma suivant ch2nh2 The reaction occurs according to the following scheme: ch2nh2
C2 H5 C2 H5
+ pcl r + pcl r
ch N = p ch N = p
_ NH-CH _ NH-CH
C H 2 5 CH25
2 —N^^ 2 —N^^
I I
C2H5 C2H5
+ +
CH30' CH30'
S02NH2 SO2NH2
COOH COOH
CH3O CH3O
S°2NH2 S°2NH2
CONH- CH F CONH- CH F
L I L I
C2H5 C2H5
3. 3.
L'exemple suivant est donné pour illustrer l'invention : The following example is given to illustrate the invention:
Dans un ballon d'un litre muni d'un agitateur, d'un réfrigérant ascendant, d'un thermomètre et d'une ampoule à brome, on introduit 27g (0,11 mpl) d'éthyl-l-aminométhyl-2-pyrrolidine et 560 ml de pyridine. 5 On agite la solution obtenue et verse goutte à goutte 5, 6 g de trichlo- In a one-liter flask equipped with a stirrer, a rising condenser, a thermometer, and a bromine funnel, 27 g (0.11 µL) of ethyl-1-aminomethyl-2-pyrrolidine and 560 mL of pyridine are introduced. The resulting solution is stirred, and 5.6 g of trichloro-
rure de phosphore (0, 04 mol) dissout dans 64 ml de pyridine tout en maintenant la température vers 20°C. Phosphorus ride (0.04 mol) dissolved in 64 ml of pyridine while maintaining the temperature around 20°C.
On laisse agiter l/2 heure à 20°C et on ajoute 14, 8 g (0, 064 mol) d'acide méthoxy-2-sulfamoyl-5-benzoi'que. On chauffe le mélange à reflux durant 4 l/2 heures et laisse reposer une nuit. La pyridine est ensuite chassée sous vide et le résidu est extrait par 200 ml d'acide chiorhydrique à 10 %. On obtient un précipité qui est chauffé vers 70-80°C et qui se dissout. Cette solution est traitée par 15 ml d'ammoniaque concentré. Le précipité formé est filtré, lavé à l'eau et séché à l'étuve à 50°C. The mixture is stirred for 30 minutes at 20°C, and 14.8 g (0.064 mol) of 2-methoxy-5-sulfamoylbenzoic acid is added. The mixture is heated under reflux for 4.5 hours and left to stand overnight. The pyridine is then removed under vacuum, and the residue is extracted with 200 mL of 10% hydrochloric acid. A precipitate is obtained, which is heated to approximately 70-80°C and dissolves. This solution is treated with 15 mL of concentrated ammonia. The resulting precipitate is filtered, washed with water, and dried in an oven at 50°C.
On obtient 16, 2 g (rendement de 74, 3 %) de N- £ (éthyl-l-pyrrolidinyl-2)- méthyl J -méthoxy~2-sulfamoyl~5-benzamide avec un point de fusion de 178° C. We obtain 16.2 g (yield of 74.3%) of N-Σ(ethyl-l-pyrrolidinyl-2)-methyl J-methoxy~2-sulfamoyl~5-benzamide with a melting point of 178° C.
Le N- j~(éthyl-l-pyrrolidinyl-2)- méthyl J -méthoxy-2-sulfamoyl-5-» 20 • ' benzamide constitue un produit intermédiaire, permettant la fabrication de principes actifs utilisables, notamment dans l'industrie phar-i ■ N-(ethyl-1-pyrrolidinyl-2)-methyl-2-methoxy-5-sulfamoyl benzamide constitutes an intermediate product, enabling the manufacture of usable active ingredients, particularly in the pharmaceutical industry.
maceutique et particulièrement en gastro-entérologie et en neurologie. / macumatics, particularly in gastroenterology and neurology.
10 10
15 15
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 |
|---|---|
| MC897A1 true MC897A1 (en) | 1972-06-22 |
Family
ID=4381427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MC956A MC897A1 (en) | 1971-08-20 | 1971-11-09 | Process for the preparation of N-Ú (ethyl-1-pyrrolidinyl-2) methyl¾ methoxy-2-sulfamoyl-5-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 ZA ZA717543A patent/ZA717543B/en unknown
- 1971-11-09 YU YU2821/71A patent/YU34286B/en unknown
- 1971-11-09 SE SE7114275A patent/SE376914B/xx 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 KR KR7101750A patent/KR780000067B1/en not_active Expired
- 1971-12-06 GB GB5649571A patent/GB1328747A/en not_active Expired
- 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 JP JP47004153A patent/JPS4829764A/ja active Pending
- 1971-12-29 CS CS9068A patent/CS177818B2/cs unknown
- 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 |
|---|---|
| DE2152370A1 (en) | 1973-02-22 |
| NO136460B (en) | 1977-05-31 |
| PL84446B1 (en) | 1976-04-30 |
| HU166567B (en) | 1975-04-28 |
| ES396718A1 (en) | 1974-05-16 |
| NL7114902A (en) | 1973-02-22 |
| CA928714A (en) | 1973-06-19 |
| IL38098A (en) | 1974-12-31 |
| SE376914B (en) | 1975-06-16 |
| IE35821L (en) | 1973-02-20 |
| AU3572171A (en) | 1973-05-24 |
| LU64275A1 (en) | 1972-06-02 |
| FR2111372A5 (en) | 1972-06-02 |
| CH547797A (en) | 1974-04-11 |
| NO136460C (en) | 1977-09-07 |
| RO62479A (en) | 1978-02-15 |
| CS177818B2 (en) | 1977-08-31 |
| DK126325B (en) | 1973-07-02 |
| GB1328747A (en) | 1973-08-30 |
| YU282171A (en) | 1978-10-31 |
| KR780000067B1 (en) | 1978-03-30 |
| BE774104A (en) | 1972-04-18 |
| JPS4829764A (en) | 1973-04-19 |
| YU34286B (en) | 1979-04-30 |
| ZM17771A1 (en) | 1972-08-21 |
| OA03928A (en) | 1975-08-14 |
| IE35821B1 (en) | 1976-05-26 |
| AT311328B (en) | 1973-11-12 |
| ZA717543B (en) | 1972-08-30 |
| IL38098A0 (en) | 1972-01-27 |
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