MC1009A1 - New process for the preparation of N- (diethylaminoethyl) 2-methoxy-4-amino-5-chlrobenzamide - Google Patents
New process for the preparation of N- (diethylaminoethyl) 2-methoxy-4-amino-5-chlrobenzamideInfo
- Publication number
- MC1009A1 MC1009A1 MC1050A MC1050A MC1009A1 MC 1009 A1 MC1009 A1 MC 1009A1 MC 1050 A MC1050 A MC 1050A MC 1050 A MC1050 A MC 1050A MC 1009 A1 MC1009 A1 MC 1009A1
- Authority
- MC
- Monaco
- Prior art keywords
- methoxy
- diethylaminoethyl
- amino
- preparation
- new process
- Prior art date
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
BREVET D'INVENTION PATENT FOR INVENTION
Déposé par la Société Anonyme dite : Filed by the public limited company known as:
SOCIETE D'ETUDES SCIENTIFIQUES ET INDUSTRIELLES DE L'ILE-DE-FRANCE SOCIETY FOR SCIENTIFIC AND INDUSTRIAL STUDIES OF ILE-DE-FRANCE
Ayant pour objet : Subject:
NOUVEAU PROCEDE DE PREPARATION DU N(DIETHYLAMINOETHYL) 2-METHOXY 4-AMINO 5-CHLOROBENZAMIDE NEW PROCESS FOR PREPARING N(DIETHYLAMINOETHYL) 2-METHOXY 4-AMINO 5-CHLOROBENZAMIDE
Priorité de la demande française : no. 72/23921, déposée le 30 juin 1972 Priority of the French application: no. 72/23921, filed on June 30, 1972
La présente invention concerne un nouveau procédé de préparation du N(diéthylaminoéthyl) 2-méthoxy 4-amino 5-chloro-benzamide (III), de ses sels d'addition avec des acides minéraux ou- organiques pharmaeeutiquemént acceptables, des sels d'ammonium quaternaires obtenus en faisant réagir ce benzamide (lll) avec un agent alcoylant. The present invention relates to a new process for preparing N(diethylaminoethyl) 2-methoxy 4-amino 5-chlorobenzamide (III), its addition salts with pharmaceutically acceptable mineral or organic acids, quaternary ammonium salts obtained by reacting this benzamide (III) with an alcoholic agent.
2 2
Le benzamide de la présente invention est obtenu en traitant l'acide 2-méthoxy 4-aminobenzolque (i) par la N, N diéthylaminoéthylènediamine en présence de chloroformiate d'éthyle pour obtenir le N(diéthylaminoéthyl) 2-méthoxy 4-aminobenzamide (il) et à chlorer ce composé par un chlorate alcalin pour obtenir le N(diéthylaminoéthyl) 2-méthoxy 4-amino 3-chlorobenzamide (III). The benzamide of the present invention is obtained by treating 2-methoxy 4-aminobenzol acid (i) with N,N diethylaminoethylenediamine in the presence of ethyl chloroformate to obtain N(diethylaminoethyl) 2-methoxy 4-aminobenzamide (il) and chlorinating this compound with an alkali chlorate to obtain N(diethylaminoethyl) 2-methoxy 4-amino 3-chlorobenzamide (III).
Le schéma de la réaction est le suivant : The reaction scheme is as follows:
10 10
15 15
COOH COOH
OCH. OCH.
'3 '3
HgNCHgCHgtT HgNCHgCHgtT
-C2H5 C2H5 -C2H5 C2H5
Ç0NHCH2CH N; Ç0NHCH2CH N;
OCH OCH
3 3
C2H5 C2H5 C2H5 C2H5
20 20
25 25
CONHCHgCHgN^ CONHCHgCHgN^
OCH- OCH-
■C2H5 C2H5 ■C2H5 C2H5
chlorate alcalin alkaline chlorate
C0NHCH2CH2N C0NHCH2CH2N
/C2H5 ^c2H5 /C2H5 ^c2H5
OCH OCH
3 3
30 30
35 35
L'exemple suivant illustre, sans la limiter, la présente invention. The following example illustrates, without limiting it, the present invention.
N(Diéthylaminoéthyl) 2-méthoxy 4-amino 5-chlorobenzamide STADB I : N(diéthylaminoéthyl) 2-méthoxy 4-aminobenzamide N(Diethylaminoethyl) 2-methoxy 4-amino 5-chlorobenzamide STADB I: N(diethylaminoethyl) 2-methoxy 4-aminobenzamide
Dans un ballon de 4 litres muni d'un agitateur mécanique, d'un thermomètre, d'un réfrigérant et d'une ampoule à brôme, on introduit 110 g (0,66 mol) d'acide 2-méthoxy 4-aminobenzolque, 2 litres de dioxanne et 92 ml de triéthylamine In a 4-liter round-bottom flask equipped with a mechanical stirrer, a thermometer, a condenser, and a bromine funnel, 110 g (0.66 mol) of 2-methoxy 4-aminobenzoic acid, 2 liters of dioxane, and 92 ml of triethylamine are introduced.
On agite dix minutes puis coule à température ambiante 72 g (0',66 mol) de chlorofonniate d'éthyle. Shake for ten minutes and then pour at room temperature 72 g (0.66 mol) of ethyl chlorofoniate.
On laisse agiter trente minutes et introduitj, en maintenant à température ambiante, 90 g (0,77 mol) de N, N 5 diéthylaminoéthylènediamine. We let it stir for thirty minutes and introduce, while maintaining at room temperature, 90 g (0.77 mol) of N,N 5 diethylaminoethylenediamine.
On agite ensuite trois heures* filtre et évapore le solvant sous vide. The mixture is then agitated for three hours*, filtered, and the solvent is evaporated under vacuum.
On ajoute 200 ml d'eau au résidu, 50 ml de soude à 40 et extrait avec 150 ml de chlorure de méthylène. La 10 solution organique séchée sur sulfate de magnésium, est filtrée - et évaporée à seo sous vide. 200 ml of water is added to the residue, along with 50 ml of sodium hydroxide solution at 40°C, and the mixture is extracted with 150 ml of methylene chloride. The resulting organic solution, dried over magnesium sulfate, is filtered and evaporated under vacuum.
On obtient 116 g de N(diéthylaminoéthyl) 2-méthoxy • 4-aminobenzamide (n $ ~ 1/5576) sous la forme d'une huile épaisse. 116 g of N(diethylaminoethyl) 2-methoxy • 4-aminobenzamide (n $ ~ 1/5576) is obtained in the form of a thick oil.
- 15 STADE II : N(diéthylaminoéthyl) 2-méthoxy 4-amino g-chloro-• benzamide - 15 STAGE II: N(diethylaminoethyl) 2-methoxy 4-amino g-chloro-• benzamide
Dans un ballon de 500 ml' muni d'un agitateur, d'un réfrigérant,, d'un thermomètre et d'une ampoule à brome, on introduit 16 g (0,06 mol) de N(diéthylaminoéthyl) 2-méthoxy 20 4-aminobenzamide, 60 ml d'acide acétique j, chauffe à 45 °C et verse 7,3 g d'anhydride acétique. In a 500 ml flask equipped with a stirrer, a condenser, a thermometer and a bromine ampoule, 16 g (0.06 mol) of N(diethylaminoethyl) 2-methoxy 20 4-aminobenzamide, 60 ml of acetic acid are introduced, heated to 45 °C and 7.3 g of acetic anhydride are added.
On laisse agiter quinze minutes à 45°C, refroidit et ajoute 18 ml d'acide ehlorhydrique à 30 $> en maintenant à température ambiante. On ajoute ensuite, goutte à goutte, en 25 maintenant à 20-25°C une solution de } g de chlorate de sodium dans 15 ml d'eau, laisse agiter quarante minutes, additionne 100 ml d'eau et la soude en quantité suffisante pour alcaliniser et saponifier. The mixture is stirred for fifteen minutes at 45°C, cooled, and 18 ml of 30% hydrochloric acid is added while maintaining room temperature. Then, a solution of 0 g of sodium chlorate in 15 ml of water is added dropwise while maintaining 20-25°C, stirred for forty minutes, and 100 ml of water and sufficient sodium hydroxide (lye) are added to alkalize and saponify.
On chauffe deux heures à reflux, refroidit, filtre 30 lave à l'eau, sèche à l'étuve à 50°C. We heat for two hours under reflux, cool, filter, wash with water, and dry in an oven at 50°C.
On obtient 14,5 S <3e N(diéthylaminoéthyl) 2-méthoxy -atnino 5-cklorobenzaraide (F ' 143-144°C). We obtain 14.5 S <3e N(diethylaminoethyl) 2-methoxy -atnino 5-chlorobenzaraide (F ' 143-144°C).
4 4
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7223921A FR2191552A5 (en) | 1972-06-30 | 1972-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MC1009A1 true MC1009A1 (en) | 1974-10-18 |
Family
ID=9101228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MC1050A MC1009A1 (en) | 1972-06-30 | 1973-06-08 | New process for the preparation of N- (diethylaminoethyl) 2-methoxy-4-amino-5-chlrobenzamide |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS4962439A (en) |
| AT (1) | AT336576B (en) |
| AU (1) | AU468903B2 (en) |
| BE (1) | BE801576A (en) |
| BG (1) | BG21855A3 (en) |
| CA (1) | CA992560A (en) |
| CH (1) | CH580063A5 (en) |
| CS (1) | CS167391B2 (en) |
| DD (1) | DD107440A5 (en) |
| DE (1) | DE2332719A1 (en) |
| ES (1) | ES408019A1 (en) |
| FR (1) | FR2191552A5 (en) |
| GB (1) | GB1398373A (en) |
| HU (1) | HU166937B (en) |
| IE (1) | IE37853B1 (en) |
| IL (1) | IL42610A (en) |
| LU (1) | LU67899A1 (en) |
| MC (1) | MC1009A1 (en) |
| PH (1) | PH11627A (en) |
| RO (1) | RO62646A2 (en) |
| SU (1) | SU515444A3 (en) |
| YU (1) | YU39020B (en) |
| ZA (1) | ZA734435B (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1960130B2 (en) * | 1968-12-02 | 1973-01-04 | Yamanouchi Pharmaceutical Co. Ltd., Tokio | Process for the preparation of N- (diethylaminoethyl) -4-amino-5-chloro-2methoxybenzamide |
-
1972
- 1972-06-30 FR FR7223921A patent/FR2191552A5/fr not_active Expired
- 1972-08-21 SU SU1821545A patent/SU515444A3/en active
- 1972-10-26 ES ES408019A patent/ES408019A1/en not_active Expired
-
1973
- 1973-06-08 MC MC1050A patent/MC1009A1/en unknown
- 1973-06-25 BG BG023966A patent/BG21855A3/en unknown
- 1973-06-26 IL IL42610A patent/IL42610A/en unknown
- 1973-06-26 GB GB3032373A patent/GB1398373A/en not_active Expired
- 1973-06-26 JP JP7271473A patent/JPS4962439A/ja active Pending
- 1973-06-26 IE IE106573A patent/IE37853B1/en unknown
- 1973-06-27 AT AT563673A patent/AT336576B/en active
- 1973-06-27 DE DE19732332719 patent/DE2332719A1/en active Pending
- 1973-06-28 PH PH14781A patent/PH11627A/en unknown
- 1973-06-28 AU AU57484/73A patent/AU468903B2/en not_active Expired
- 1973-06-28 DD DD17190473A patent/DD107440A5/xx unknown
- 1973-06-28 LU LU67899A patent/LU67899A1/xx unknown
- 1973-06-28 HU HUSO001091 patent/HU166937B/hu unknown
- 1973-06-28 BE BE1005201A patent/BE801576A/en not_active IP Right Cessation
- 1973-06-29 ZA ZA734435A patent/ZA734435B/en unknown
- 1973-06-29 RO RO7529873A patent/RO62646A2/en unknown
- 1973-06-29 CH CH957273A patent/CH580063A5/xx not_active IP Right Cessation
- 1973-06-29 CA CA175,222A patent/CA992560A/en not_active Expired
- 1973-06-29 YU YU176973A patent/YU39020B/en unknown
- 1973-06-29 CS CS474973A patent/CS167391B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2191552A5 (en) | 1974-02-01 |
| AU468903B2 (en) | 1976-01-29 |
| CH580063A5 (en) | 1976-09-30 |
| YU39020B (en) | 1984-02-29 |
| CS167391B2 (en) | 1976-04-29 |
| ES408019A1 (en) | 1975-11-01 |
| IL42610A0 (en) | 1973-08-29 |
| HU166937B (en) | 1975-06-28 |
| DD107440A5 (en) | 1974-08-05 |
| AU5748473A (en) | 1975-01-09 |
| JPS4962439A (en) | 1974-06-17 |
| AT336576B (en) | 1977-05-10 |
| BG21855A3 (en) | 1976-09-20 |
| LU67899A1 (en) | 1974-08-19 |
| PH11627A (en) | 1978-04-12 |
| YU176973A (en) | 1982-02-28 |
| IE37853L (en) | 1973-12-30 |
| IE37853B1 (en) | 1977-10-26 |
| SU515444A3 (en) | 1976-05-25 |
| ATA563673A (en) | 1976-09-15 |
| GB1398373A (en) | 1975-06-18 |
| RO62646A2 (en) | 1978-02-15 |
| ZA734435B (en) | 1974-05-29 |
| BE801576A (en) | 1973-12-28 |
| CA992560A (en) | 1976-07-06 |
| DE2332719A1 (en) | 1974-01-10 |
| IL42610A (en) | 1976-03-31 |
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