DE2332719A1 - Verfahren zur herstellung von n(diaethylaminoaethyl)-2-methoxy-4-amino5-chlorbenzamid - Google Patents
Verfahren zur herstellung von n(diaethylaminoaethyl)-2-methoxy-4-amino5-chlorbenzamidInfo
- Publication number
- DE2332719A1 DE2332719A1 DE19732332719 DE2332719A DE2332719A1 DE 2332719 A1 DE2332719 A1 DE 2332719A1 DE 19732332719 DE19732332719 DE 19732332719 DE 2332719 A DE2332719 A DE 2332719A DE 2332719 A1 DE2332719 A1 DE 2332719A1
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- chlorobenzamide
- diethylaminoethyl
- diaethylaminoaethyl
- amino5
- 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
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims description 6
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 claims description 5
- OLJXRTRRJSMURJ-UHFFFAOYSA-N 4-amino-2-methoxybenzoic acid Chemical compound COC1=CC(N)=CC=C1C(O)=O OLJXRTRRJSMURJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 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
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- AQOCQFLDHPSJLR-UHFFFAOYSA-N 4-amino-n-[2-(diethylamino)ethyl]-2-methoxybenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(N)C=C1OC AQOCQFLDHPSJLR-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-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
- -1 ethylaminoethyl Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QIKYZXDTTPVVAC-UHFFFAOYSA-N 4-Aminobenzamide Chemical compound NC(=O)C1=CC=C(N)C=C1 QIKYZXDTTPVVAC-UHFFFAOYSA-N 0.000 description 1
- ASQGSHOSTVLLHK-UHFFFAOYSA-N 4-amino-5-chloro-2-ethoxybenzamide Chemical compound CCOC1=CC(N)=C(Cl)C=C1C(N)=O ASQGSHOSTVLLHK-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- 238000001035 drying Methods 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7223921A FR2191552A5 (en:Method) | 1972-06-30 | 1972-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2332719A1 true DE2332719A1 (de) | 1974-01-10 |
Family
ID=9101228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732332719 Pending DE2332719A1 (de) | 1972-06-30 | 1973-06-27 | Verfahren zur herstellung von n(diaethylaminoaethyl)-2-methoxy-4-amino5-chlorbenzamid |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS4962439A (en:Method) |
| AT (1) | AT336576B (en:Method) |
| AU (1) | AU468903B2 (en:Method) |
| BE (1) | BE801576A (en:Method) |
| BG (1) | BG21855A3 (en:Method) |
| CA (1) | CA992560A (en:Method) |
| CH (1) | CH580063A5 (en:Method) |
| CS (1) | CS167391B2 (en:Method) |
| DD (1) | DD107440A5 (en:Method) |
| DE (1) | DE2332719A1 (en:Method) |
| ES (1) | ES408019A1 (en:Method) |
| FR (1) | FR2191552A5 (en:Method) |
| GB (1) | GB1398373A (en:Method) |
| HU (1) | HU166937B (en:Method) |
| IE (1) | IE37853B1 (en:Method) |
| IL (1) | IL42610A (en:Method) |
| LU (1) | LU67899A1 (en:Method) |
| MC (1) | MC1009A1 (en:Method) |
| PH (1) | PH11627A (en:Method) |
| RO (1) | RO62646A2 (en:Method) |
| SU (1) | SU515444A3 (en:Method) |
| YU (1) | YU39020B (en:Method) |
| ZA (1) | ZA734435B (en:Method) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1960130B2 (de) * | 1968-12-02 | 1973-01-04 | Yamanouchi Pharmaceutical Co. Ltd., Tokio | Verfahren zur Herstellung von N-(Diäthylaminoäthyl)-4-amino-5-chlor-2methoxybenzamid |
-
1972
- 1972-06-30 FR FR7223921A patent/FR2191552A5/fr not_active Expired
- 1972-08-21 SU SU1821545A patent/SU515444A3/ru active
- 1972-10-26 ES ES408019A patent/ES408019A1/es not_active Expired
-
1973
- 1973-06-08 MC MC1050A patent/MC1009A1/xx unknown
- 1973-06-25 BG BG023966A patent/BG21855A3/xx 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 IL IL42610A patent/IL42610A/en unknown
- 1973-06-26 IE IE106573A patent/IE37853B1/xx unknown
- 1973-06-27 AT AT563673A patent/AT336576B/de active
- 1973-06-27 DE DE19732332719 patent/DE2332719A1/de active Pending
- 1973-06-28 LU LU67899A patent/LU67899A1/xx unknown
- 1973-06-28 DD DD17190473A patent/DD107440A5/xx unknown
- 1973-06-28 AU AU57484/73A patent/AU468903B2/en not_active Expired
- 1973-06-28 PH PH14781A patent/PH11627A/en unknown
- 1973-06-28 BE BE1005201A patent/BE801576A/xx not_active IP Right Cessation
- 1973-06-28 HU HUSO001091 patent/HU166937B/hu unknown
- 1973-06-29 ZA ZA734435A patent/ZA734435B/xx unknown
- 1973-06-29 CA CA175,222A patent/CA992560A/fr not_active Expired
- 1973-06-29 CH CH957273A patent/CH580063A5/xx not_active IP Right Cessation
- 1973-06-29 CS CS474973A patent/CS167391B2/cs unknown
- 1973-06-29 RO RO7529873A patent/RO62646A2/ro unknown
- 1973-06-29 YU YU176973A patent/YU39020B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS167391B2 (en:Method) | 1976-04-29 |
| ATA563673A (de) | 1976-09-15 |
| ES408019A1 (es) | 1975-11-01 |
| CA992560A (fr) | 1976-07-06 |
| IL42610A0 (en) | 1973-08-29 |
| YU39020B (en) | 1984-02-29 |
| CH580063A5 (en:Method) | 1976-09-30 |
| IE37853L (en) | 1973-12-30 |
| AU468903B2 (en) | 1976-01-29 |
| SU515444A3 (ru) | 1976-05-25 |
| GB1398373A (en) | 1975-06-18 |
| RO62646A2 (fr) | 1978-02-15 |
| JPS4962439A (en:Method) | 1974-06-17 |
| ZA734435B (en) | 1974-05-29 |
| DD107440A5 (en:Method) | 1974-08-05 |
| HU166937B (en:Method) | 1975-06-28 |
| BG21855A3 (bg) | 1976-09-20 |
| PH11627A (en) | 1978-04-12 |
| BE801576A (fr) | 1973-12-28 |
| MC1009A1 (fr) | 1974-10-18 |
| IL42610A (en) | 1976-03-31 |
| LU67899A1 (en:Method) | 1974-08-19 |
| FR2191552A5 (en:Method) | 1974-02-01 |
| AT336576B (de) | 1977-05-10 |
| YU176973A (en) | 1982-02-28 |
| AU5748473A (en) | 1975-01-09 |
| IE37853B1 (en) | 1977-10-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |