DE2331262A1 - Verfahren zur herstellung von n-(diaethylaminoaethyl)-2-methoxy-4-amino-5-chlorbenzamid - Google Patents
Verfahren zur herstellung von n-(diaethylaminoaethyl)-2-methoxy-4-amino-5-chlorbenzamidInfo
- Publication number
- DE2331262A1 DE2331262A1 DE2331262A DE2331262A DE2331262A1 DE 2331262 A1 DE2331262 A1 DE 2331262A1 DE 2331262 A DE2331262 A DE 2331262A DE 2331262 A DE2331262 A DE 2331262A DE 2331262 A1 DE2331262 A1 DE 2331262A1
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- chlorobenzamide
- amino
- acetamino
- preparation
- 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 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 4
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 3
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 claims description 2
- -1 2-methoxy-4-acetamino-5-chlorobenzoic acid halide Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- YBCOOGQGBVDQSB-UHFFFAOYSA-N 4-acetamido-5-chloro-2-methoxybenzoyl chloride Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1C(Cl)=O YBCOOGQGBVDQSB-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- UJBLIKMTKGJYLA-UHFFFAOYSA-N 4-acetamido-5-chloro-N-(2-chloroethyl)-2-methoxybenzamide Chemical compound ClCCNC(C1=C(C=C(C(=C1)Cl)NC(C)=O)OC)=O UJBLIKMTKGJYLA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- JSKOIKWLXHXATD-UHFFFAOYSA-N 2-chloroethanamine hypochlorous acid Chemical compound ClO.ClCCN JSKOIKWLXHXATD-UHFFFAOYSA-N 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7222695A FR2281353A1 (fr) | 1972-06-22 | 1972-06-22 | Nouveau procede de preparation du n(diethylaminoethyl) 2-methoxy 4-amino 5-chlorobenzamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2331262A1 true DE2331262A1 (de) | 1974-01-17 |
Family
ID=9100674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2331262A Pending DE2331262A1 (de) | 1972-06-22 | 1973-06-19 | Verfahren zur herstellung von n-(diaethylaminoaethyl)-2-methoxy-4-amino-5-chlorbenzamid |
Country Status (20)
| Country | Link |
|---|---|
| KR (1) | KR780000254B1 (OSRAM) |
| AT (1) | AT350045B (OSRAM) |
| AU (1) | AU468922B2 (OSRAM) |
| BE (1) | BE801037A (OSRAM) |
| BG (1) | BG21398A3 (OSRAM) |
| CA (1) | CA992559A (OSRAM) |
| CH (1) | CH570971A5 (OSRAM) |
| CS (1) | CS168034B2 (OSRAM) |
| DD (1) | DD108283A5 (OSRAM) |
| DE (1) | DE2331262A1 (OSRAM) |
| ES (1) | ES416099A1 (OSRAM) |
| FR (1) | FR2281353A1 (OSRAM) |
| GB (1) | GB1395132A (OSRAM) |
| HU (1) | HU166935B (OSRAM) |
| IE (1) | IE37822B1 (OSRAM) |
| IL (1) | IL42546A (OSRAM) |
| LU (1) | LU67829A1 (OSRAM) |
| MC (1) | MC1008A1 (OSRAM) |
| YU (1) | YU36692B (OSRAM) |
| ZA (1) | ZA734193B (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2528037A1 (fr) * | 1982-06-08 | 1983-12-09 | Centre Nat Rech Scient | Procede de preparation de phenolamides |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4808624A (en) * | 1984-06-28 | 1989-02-28 | Bristol-Myers Company | Pharmacologically active substituted benzamides |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1233877B (de) * | 1961-07-25 | 1967-02-09 | Ile De France | Verfahren zur Herstellung von substituierten N-(tert. Aminoalkyl)-benzamiden |
-
1972
- 1972-06-22 FR FR7222695A patent/FR2281353A1/fr active Granted
-
1973
- 1973-06-08 MC MC1049A patent/MC1008A1/fr unknown
- 1973-06-13 GB GB2820473A patent/GB1395132A/en not_active Expired
- 1973-06-18 HU HUSO1087A patent/HU166935B/hu unknown
- 1973-06-18 BG BG023904A patent/BG21398A3/xx unknown
- 1973-06-18 BE BE1005165A patent/BE801037A/xx not_active IP Right Cessation
- 1973-06-19 CA CA174,389A patent/CA992559A/fr not_active Expired
- 1973-06-19 AT AT536973A patent/AT350045B/de not_active IP Right Cessation
- 1973-06-19 CS CS4411A patent/CS168034B2/cs unknown
- 1973-06-19 IE IE1006/73A patent/IE37822B1/xx unknown
- 1973-06-19 IL IL42546A patent/IL42546A/en unknown
- 1973-06-19 DE DE2331262A patent/DE2331262A1/de active Pending
- 1973-06-20 LU LU67829A patent/LU67829A1/xx unknown
- 1973-06-20 ES ES416099A patent/ES416099A1/es not_active Expired
- 1973-06-20 KR KR7300972A patent/KR780000254B1/ko not_active Expired
- 1973-06-20 DD DD171686A patent/DD108283A5/xx unknown
- 1973-06-21 CH CH906473A patent/CH570971A5/xx not_active IP Right Cessation
- 1973-06-21 AU AU57213/73A patent/AU468922B2/en not_active Expired
- 1973-06-21 ZA ZA734193A patent/ZA734193B/xx unknown
- 1973-06-22 YU YU1693/73A patent/YU36692B/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2528037A1 (fr) * | 1982-06-08 | 1983-12-09 | Centre Nat Rech Scient | Procede de preparation de phenolamides |
| WO1983004411A1 (fr) * | 1982-06-08 | 1983-12-22 | Centre National De La Recherche Scientifique (Cnrs | Procede de preparation de phenolamides |
| EP0097096A1 (fr) * | 1982-06-08 | 1983-12-28 | Centre National De La Recherche Scientifique (Cnrs) | Procédé de préparation de phénolamides |
Also Published As
| Publication number | Publication date |
|---|---|
| YU36692B (en) | 1984-08-31 |
| IL42546A (en) | 1976-11-30 |
| FR2281353A1 (fr) | 1976-03-05 |
| CA992559A (fr) | 1976-07-06 |
| CH570971A5 (OSRAM) | 1975-12-31 |
| AU468922B2 (en) | 1976-01-29 |
| CS168034B2 (OSRAM) | 1976-05-28 |
| GB1395132A (en) | 1975-05-21 |
| IE37822B1 (en) | 1977-10-26 |
| ZA734193B (en) | 1974-06-26 |
| BG21398A3 (bg) | 1976-05-20 |
| AU5721373A (en) | 1975-01-09 |
| ATA536973A (de) | 1978-10-15 |
| FR2281353B1 (OSRAM) | 1979-03-30 |
| LU67829A1 (OSRAM) | 1974-07-10 |
| KR780000254B1 (en) | 1978-07-06 |
| ES416099A1 (es) | 1976-02-16 |
| IE37822L (en) | 1973-12-22 |
| YU169373A (en) | 1982-06-18 |
| DD108283A5 (OSRAM) | 1974-09-12 |
| AT350045B (de) | 1979-05-10 |
| BE801037A (fr) | 1973-12-18 |
| HU166935B (OSRAM) | 1975-06-28 |
| MC1008A1 (fr) | 1974-10-18 |
| IL42546A0 (en) | 1973-08-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |