IL42610A - The preparation of n-(diethylaminoethyl)2-methoxy-4-amino-5-chlorobenzamide - Google Patents
The preparation of n-(diethylaminoethyl)2-methoxy-4-amino-5-chlorobenzamideInfo
- Publication number
- IL42610A IL42610A IL42610A IL4261073A IL42610A IL 42610 A IL42610 A IL 42610A IL 42610 A IL42610 A IL 42610A IL 4261073 A IL4261073 A IL 4261073A IL 42610 A IL42610 A IL 42610A
- Authority
- IL
- Israel
- Prior art keywords
- methoxy
- chlorobenzamide
- amino
- diethylamino
- diethylaminoethyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title description 3
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims description 7
- -1 alkali metal chlorate Chemical class 0.000 claims description 4
- XTEGARKTQYYJKE-UHFFFAOYSA-M chlorate Inorganic materials [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical group CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 claims 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229960004050 aminobenzoic acid Drugs 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HGDWUJQEOCVOKM-UHFFFAOYSA-N 2-(2,2-diethylhydrazinyl)ethanamine Chemical compound CCN(CC)NCCN HGDWUJQEOCVOKM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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)
Description
The preparation of ET 40735 present invention concerns a novel method of preparing its of addition with pharmaceutically acceptable mineral or organic and the quaternary ammonium salts produced by reacting the benzamide vith an alkylating Israel Patent Specification 17500 discloses a method for the preparation of substituted in which the amidification is effected by reacting a benzoic acid chloride with an and British patent specification another herein a benzoic acid ester is reacted with an amine and the chlorination carried out with Another method in which the amidification is effected by reacting a benzoic acid ester with an amine is described in The benzamide of the present invention is produced by treating benzoic acid by in the presence of ethyl chloroformiate to produce benzamide and chlorinating said compound by an alkaline chlorate to produce The reaction dia ram is as STAGE 110 g of 2 litres of dioxan and 92 ml of triethylamine are introduced into a 4 litre balloon flask provided a mechanical a a cooler and a dropping The mixture is agitated for 10 minutes and then g of ethyl is poured in at ambient The mixture is agitated for a further minutes and 90 g mole of N diethylaminoethylenediamine is vith the temperature being maintained at ambient The mixture is then agitated for 3 followed by and the solvent is evaporated under 200 ml of water is added to the and ml of sodium and the solution is extracted vith 150 ml of methylene The organic solution is dried on magnesium filtered and evaporated to dryness under g of 27 C is produced in the form of a thick STAGE 16 g of round and 60 ml of acetic are introduced into a 500 flask provided vith an a a thermometer and a dropping and heated to 45 of acetic anhydride is then poured The mixture is agitated for 15 minutes at 45 followed by and 18 ml of hydrochloric acid is then the temperature being at ambient A solution of of sodium chlorate in 15 of water is then added with the temperature being maintained at from 20 to 25 the solution is then agitated for 40 followed by the addition of 100 ml of and sodium hydroxide in an amount sufficient to and Ileating under reflux is then effected for 2 followed by vatcr and drying in a drying oven at g of is 9 insufficientOCRQuality
Claims (4)
1. A method of preparing N- 2-(N' , '-diethylamino) ethyl/ 2-methoxy-4-araino-5-chlorobenzamide, which has the formula: and its acid-addition salts with pharmaceutically acceptable mineral or organic acids and quaternary ammonium salts, that comprises reacting Ν,Ν-diethylethylenediamine with 2- ethoxy-4~aminobenzoic acid in the presence of ethyl chloroformate to produce N-diethylaminoethyl-2-methoxy-4- in the presence of HCl aminobenzamide and reacting the latter compound/with an alkali metal chlorate to produce N- 2-(N' ,N'-diethylamino)ethyl7- 2-methoxy-4-amino-5-chlorobenzamide, and optionally reacting the latter with an acid or a quaternizing agent to form a salt.
2. A method according to claim 1 in which the alkali metal chlorate is sodium chlorate.
3. A method according to claim 1 substantially as hereinbefore described in the foregoing Example *
4. N- 2- (N ' , N · -diethylamino ) ethyl7-2-methoxy-4-amino-5-chlorobenzamide when prepared by a method as claimed in any one of the preceding claims. •
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7223921A FR2191552A5 (en) | 1972-06-30 | 1972-06-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42610A0 IL42610A0 (en) | 1973-08-29 |
| IL42610A true IL42610A (en) | 1976-03-31 |
Family
ID=9101228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42610A IL42610A (en) | 1972-06-30 | 1973-06-26 | The preparation of n-(diethylaminoethyl)2-methoxy-4-amino-5-chlorobenzamide |
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 JP JP7271473A patent/JPS4962439A/ja active Pending
- 1973-06-26 IE IE106573A patent/IE37853B1/en unknown
- 1973-06-26 GB GB3032373A patent/GB1398373A/en not_active Expired
- 1973-06-27 DE DE19732332719 patent/DE2332719A1/en active Pending
- 1973-06-27 AT AT563673A patent/AT336576B/en active
- 1973-06-28 PH PH14781A patent/PH11627A/en unknown
- 1973-06-28 BE BE1005201A patent/BE801576A/en not_active IP Right Cessation
- 1973-06-28 HU HUSO001091 patent/HU166937B/hu unknown
- 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
- 1973-06-29 CH CH957273A patent/CH580063A5/xx not_active IP Right Cessation
- 1973-06-29 ZA ZA734435A patent/ZA734435B/en unknown
- 1973-06-29 CS CS474973A patent/CS167391B2/cs unknown
- 1973-06-29 RO RO7529873A patent/RO62646A2/en unknown
- 1973-06-29 CA CA175,222A patent/CA992560A/en not_active Expired
- 1973-06-29 YU YU176973A patent/YU39020B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU176973A (en) | 1982-02-28 |
| BG21855A3 (en) | 1976-09-20 |
| LU67899A1 (en) | 1974-08-19 |
| ZA734435B (en) | 1974-05-29 |
| DD107440A5 (en) | 1974-08-05 |
| DE2332719A1 (en) | 1974-01-10 |
| CH580063A5 (en) | 1976-09-30 |
| AU5748473A (en) | 1975-01-09 |
| CA992560A (en) | 1976-07-06 |
| AT336576B (en) | 1977-05-10 |
| AU468903B2 (en) | 1976-01-29 |
| CS167391B2 (en) | 1976-04-29 |
| PH11627A (en) | 1978-04-12 |
| IL42610A0 (en) | 1973-08-29 |
| RO62646A2 (en) | 1978-02-15 |
| GB1398373A (en) | 1975-06-18 |
| SU515444A3 (en) | 1976-05-25 |
| IE37853L (en) | 1973-12-30 |
| MC1009A1 (en) | 1974-10-18 |
| YU39020B (en) | 1984-02-29 |
| FR2191552A5 (en) | 1974-02-01 |
| BE801576A (en) | 1973-12-28 |
| ATA563673A (en) | 1976-09-15 |
| HU166937B (en) | 1975-06-28 |
| ES408019A1 (en) | 1975-11-01 |
| JPS4962439A (en) | 1974-06-17 |
| IE37853B1 (en) | 1977-10-26 |
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