MC897A1 - Procédé de préparation du N-Ú(ethyl-1-pyrrolidinyl-2) methyl¾ methoxy-2-sulfamoyl-5-benzamide - Google Patents
Procédé de préparation du 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
.Procède de préparation du N- jjéthyl-l-pyrrolidinyl-2)- méthylj -méthoxy- 2-sulfamoyl-5-benzamide
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.
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.
Comme milieu de réaction on utilise de préférence la pyridine.
La réaction-se produit selon le schéma suivant ch2nh2
C2 H5
+ pcl r
ch N = p
_ NH-CH
C H 2 5
2 —N^^
I
C2H5
+
CH30'
S02NH2
COOH
CH3O
S°2NH2
CONH- CH F
L I
C2H5
3.
L'exemple suivant est donné pour illustrer l'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-
rure de phosphore (0, 04 mol) dissout dans 64 ml de pyridine tout en maintenant la température vers 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.
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.
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 ■
maceutique et particulièrement en gastro-entérologie et en neurologie. /
10
15
Claims (1)
- 'H' \*-r■JN' *-''If ^fT/ï-.. t-ty". "■ V<*: :K'"«i|s^ÉiiÉiip3;sr 's asfSiS||alB#S«\:;s *u'i"' /*■»,"Sresume '(.L'invention a pour objet :Un procédé de préparation du N- £ (éthyl-l-pyrrolidinyl~ 2)-méthyl J -méthoxy-2-sulfamoyl-5-benzamide caractérisé par les points sui-vants considérés isolément ou en combinaison :On fait réagir l'acide méthoxy-2-sulfamoyl-5-benzoi'que et l'éthyl-l-aminbméthyl-2-pyrrolidine en présence de trichlorure de phosphore.On utilise la pyridine comme milieu de réaction.9=<-w(r {*_ /^<30V', r^s^.6 9^-Pau* ProcuratlefiûJf vd */^s^Ay t ,
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1226771A CH547797A (de) | 1971-08-20 | 1971-08-20 | Verfahren zur herstellung von n - ((1-aethyl-pyrrolidinyl2)-methyl) -2-methoxy-5-sulfamoyl-benzamid. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MC897A1 true MC897A1 (fr) | 1972-06-22 |
Family
ID=4381427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MC956A MC897A1 (fr) | 1971-08-20 | 1971-11-09 | Procédé de préparation du N-Ú(ethyl-1-pyrrolidinyl-2) methyl¾ methoxy-2-sulfamoyl-5-benzamide |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS4829764A (fr) |
| KR (1) | KR780000067B1 (fr) |
| AT (1) | AT311328B (fr) |
| BE (1) | BE774104A (fr) |
| CA (1) | CA928714A (fr) |
| CH (1) | CH547797A (fr) |
| CS (1) | CS177818B2 (fr) |
| DE (1) | DE2152370A1 (fr) |
| DK (1) | DK126325B (fr) |
| ES (1) | ES396718A1 (fr) |
| FR (1) | FR2111372A5 (fr) |
| GB (1) | GB1328747A (fr) |
| HU (1) | HU166567B (fr) |
| IE (1) | IE35821B1 (fr) |
| IL (1) | IL38098A (fr) |
| LU (1) | LU64275A1 (fr) |
| MC (1) | MC897A1 (fr) |
| NL (1) | NL7114902A (fr) |
| NO (1) | NO136460C (fr) |
| OA (1) | OA03928A (fr) |
| PL (1) | PL84446B1 (fr) |
| RO (1) | RO62479A (fr) |
| SE (1) | SE376914B (fr) |
| YU (1) | YU34286B (fr) |
| ZA (1) | ZA717543B (fr) |
| ZM (1) | ZM17771A1 (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2252336B1 (fr) * | 1973-11-27 | 1977-03-04 | Ile De France | |
| JPS5170235A (fr) * | 1974-12-16 | 1976-06-17 | Toyo Aluminium Kk | |
| NZ186175A (en) * | 1977-01-27 | 1980-03-05 | Shionogi & Co | Meta-sulphonamidobenzamide derivatives |
| WO1991017144A1 (fr) * | 1990-05-02 | 1991-11-14 | Yoshitomi Pharmaceutical Industries, Ltd. | Compose amide, utilisation pharmaceutique de ce compose et nouvelles pyrrolidinemethyl-amines 1-substituee |
-
1971
- 1971-08-20 CH CH1226771A patent/CH547797A/xx not_active IP Right Cessation
- 1971-10-14 FR FR7136941A patent/FR2111372A5/fr not_active Expired
- 1971-10-18 BE BE774104A patent/BE774104A/fr not_active IP Right Cessation
- 1971-10-21 DE DE19712152370 patent/DE2152370A1/de active Pending
- 1971-10-28 NL NL7114902A patent/NL7114902A/xx unknown
- 1971-11-05 ES ES396718A patent/ES396718A1/es not_active Expired
- 1971-11-08 IL IL38098A patent/IL38098A/en unknown
- 1971-11-08 CA CA127136A patent/CA928714A/en not_active Expired
- 1971-11-09 ZA ZA717543A patent/ZA717543B/xx unknown
- 1971-11-09 SE SE7114275A patent/SE376914B/xx unknown
- 1971-11-09 MC MC956A patent/MC897A1/fr unknown
- 1971-11-09 YU YU2821/71A patent/YU34286B/xx unknown
- 1971-11-16 LU LU64275D patent/LU64275A1/xx unknown
- 1971-11-18 IE IE1459/71A patent/IE35821B1/xx unknown
- 1971-11-29 DK DK584371AA patent/DK126325B/da 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/ko not_active Expired
- 1971-12-06 GB GB5649571A patent/GB1328747A/en not_active Expired
- 1971-12-07 OA OA54434A patent/OA03928A/fr unknown
- 1971-12-08 PL PL1971152013A patent/PL84446B1/pl unknown
- 1971-12-10 AT AT1064371A patent/AT311328B/de 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/no unknown
-
1972
- 1972-01-15 RO RO7200069412A patent/RO62479A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK126325B (da) | 1973-07-02 |
| AU3572171A (en) | 1973-05-24 |
| NL7114902A (fr) | 1973-02-22 |
| CA928714A (en) | 1973-06-19 |
| ZA717543B (en) | 1972-08-30 |
| CS177818B2 (fr) | 1977-08-31 |
| NO136460C (no) | 1977-09-07 |
| ES396718A1 (es) | 1974-05-16 |
| RO62479A (fr) | 1978-02-15 |
| IL38098A (en) | 1974-12-31 |
| KR780000067B1 (en) | 1978-03-30 |
| BE774104A (fr) | 1972-04-18 |
| DE2152370A1 (de) | 1973-02-22 |
| AT311328B (de) | 1973-11-12 |
| FR2111372A5 (fr) | 1972-06-02 |
| YU34286B (en) | 1979-04-30 |
| OA03928A (fr) | 1975-08-14 |
| LU64275A1 (fr) | 1972-06-02 |
| JPS4829764A (fr) | 1973-04-19 |
| SE376914B (fr) | 1975-06-16 |
| ZM17771A1 (fr) | 1972-08-21 |
| PL84446B1 (fr) | 1976-04-30 |
| IE35821B1 (en) | 1976-05-26 |
| HU166567B (fr) | 1975-04-28 |
| IL38098A0 (en) | 1972-01-27 |
| IE35821L (en) | 1973-02-20 |
| GB1328747A (en) | 1973-08-30 |
| CH547797A (de) | 1974-04-11 |
| NO136460B (fr) | 1977-05-31 |
| YU282171A (en) | 1978-10-31 |
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