DE1543893C3 - Verfahren zur Herstellung von N-(Diäthylaminoäthyl)-2-methoxy-4-amino-5-chlorbenzamid - Google Patents
Verfahren zur Herstellung von N-(Diäthylaminoäthyl)-2-methoxy-4-amino-5-chlorbenzamidInfo
- Publication number
- DE1543893C3 DE1543893C3 DE1543893A DE1543893A DE1543893C3 DE 1543893 C3 DE1543893 C3 DE 1543893C3 DE 1543893 A DE1543893 A DE 1543893A DE 1543893 A DE1543893 A DE 1543893A DE 1543893 C3 DE1543893 C3 DE 1543893C3
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- amino
- diethylaminoethyl
- nitro
- chlorobenzamide
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims 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 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- GHFCSIIJUBBDQF-UHFFFAOYSA-N 5-chloro-2-methoxy-4-nitrobenzonitrile Chemical compound COC1=C(C#N)C=C(C(=C1)[N+](=O)[O-])Cl GHFCSIIJUBBDQF-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- PVUYBBJPARWTJY-UHFFFAOYSA-N 5-chloro-n-[2-(diethylamino)ethyl]-2-methoxy-4-nitrobenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C([N+]([O-])=O)C=C1OC PVUYBBJPARWTJY-UHFFFAOYSA-N 0.000 claims description 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 3
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 3
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 3
- 238000000297 Sandmeyer reaction Methods 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- POKAEVPBUOLQIY-UHFFFAOYSA-N 5-chloro-2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=C(Cl)C=C1N POKAEVPBUOLQIY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OSAYFGJUEOYRHY-UHFFFAOYSA-N 4-chloro-1-methoxy-2-nitrobenzene Chemical compound COC1=CC=C(Cl)C=C1[N+]([O-])=O OSAYFGJUEOYRHY-UHFFFAOYSA-N 0.000 description 1
- VJLQAJYDEDLSGO-UHFFFAOYSA-N 4-chloro-2-methoxy-5-nitroaniline Chemical compound COC1=CC(Cl)=C([N+]([O-])=O)C=C1N VJLQAJYDEDLSGO-UHFFFAOYSA-N 0.000 description 1
- NWSIFTLPLKCTSX-UHFFFAOYSA-N 4-chloro-2-nitrophenol Chemical compound OC1=CC=C(Cl)C=C1[N+]([O-])=O NWSIFTLPLKCTSX-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- ZGHDLDHWTRBXPO-UHFFFAOYSA-N 5-chloro-2-methoxy-4-nitrobenzoic acid Chemical compound COC1=CC([N+]([O-])=O)=C(Cl)C=C1C(O)=O ZGHDLDHWTRBXPO-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002050 international nonproprietary name Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- DQWAYGCKXVIMQW-UHFFFAOYSA-N methyl 5-chloro-2-methoxy-4-nitrobenzoate Chemical compound COC1=C(C(=O)OC)C=C(C(=C1)[N+](=O)[O-])Cl DQWAYGCKXVIMQW-UHFFFAOYSA-N 0.000 description 1
- 229960004503 metoclopramide Drugs 0.000 description 1
- KQGNEXQCCNUZMT-UHFFFAOYSA-N n-(5-chloro-2-methoxy-4-nitrophenyl)acetamide Chemical compound COC1=CC([N+]([O-])=O)=C(Cl)C=C1NC(C)=O KQGNEXQCCNUZMT-UHFFFAOYSA-N 0.000 description 1
- WKZLKZPMUWYXTK-UHFFFAOYSA-N n-(5-chloro-2-methoxyphenyl)acetamide Chemical compound COC1=CC=C(Cl)C=C1NC(C)=O WKZLKZPMUWYXTK-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- 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
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/50—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19661793772 DE1793772B2 (de) | 1965-12-27 | 1966-12-16 | N-(Diäthylaminoäthyl)-2-methoxy-4amino-5-chlorbenzamid-Monohydrochlorid, Verfahren zu dessen Herstellung sowie diese Verbindung enthaltende Arzneimittel Ausscheidung aus: 1543893 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR43874A FR1513226A (fr) | 1965-12-27 | 1965-12-27 | Nouveau procédé de préparation de benzamides substitués |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1543893A1 DE1543893A1 (de) | 1970-02-05 |
| DE1543893B2 DE1543893B2 (de) | 1974-10-10 |
| DE1543893C3 true DE1543893C3 (de) | 1975-05-22 |
Family
ID=8596948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1543893A Expired DE1543893C3 (de) | 1965-12-27 | 1966-12-16 | Verfahren zur Herstellung von N-(Diäthylaminoäthyl)-2-methoxy-4-amino-5-chlorbenzamid |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS546539B1 (cs) |
| BE (1) | BE688790A (cs) |
| CH (1) | CH475949A (cs) |
| DE (1) | DE1543893C3 (cs) |
| ES (1) | ES333713A1 (cs) |
| FR (1) | FR1513226A (cs) |
| GB (1) | GB1153796A (cs) |
| IL (1) | IL26895A (cs) |
| OA (1) | OA02159A (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54148743A (en) * | 1978-05-12 | 1979-11-21 | Asahi Chem Ind Co Ltd | Production of methoclopramide |
| JPS6058224B2 (ja) | 1978-07-31 | 1985-12-19 | 旭化成株式会社 | メトクロプラミドの製造方法 |
| FR2460923A1 (fr) * | 1979-07-06 | 1981-01-30 | Ile De France | Nouveau procede de preparation d'acides 2-methoxy-4-amino-5-alkylsulfonyl benzoiques |
| CN111349052B (zh) * | 2020-04-07 | 2021-02-12 | 福建海西新药创制有限公司 | 一种枸橼酸莫沙必利的合成方法 |
-
1965
- 1965-12-27 FR FR43874A patent/FR1513226A/fr not_active Expired
-
1966
- 1966-10-20 OA OA52632A patent/OA02159A/xx unknown
- 1966-10-24 BE BE688790D patent/BE688790A/xx not_active IP Right Cessation
- 1966-11-11 ES ES0333713A patent/ES333713A1/es not_active Expired
- 1966-11-11 GB GB50701/66A patent/GB1153796A/en not_active Expired
- 1966-11-15 CH CH1637766A patent/CH475949A/fr not_active IP Right Cessation
- 1966-11-20 IL IL26895A patent/IL26895A/xx unknown
- 1966-12-16 DE DE1543893A patent/DE1543893C3/de not_active Expired
-
1972
- 1972-06-05 JP JP5640172A patent/JPS546539B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES333713A1 (es) | 1967-10-01 |
| OA02159A (fr) | 1970-05-05 |
| DE1543893A1 (de) | 1970-02-05 |
| BE688790A (cs) | 1967-04-24 |
| CH475949A (fr) | 1969-07-31 |
| GB1153796A (en) | 1969-05-29 |
| IL26895A (en) | 1971-08-25 |
| JPS546539B1 (cs) | 1979-03-29 |
| FR1513226A (fr) | 1968-02-16 |
| DE1543893B2 (de) | 1974-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |