DE2409388A1 - PROCESS FOR THE PREPARATION OF N (DIATHYLAMINOAETHYL) -2-METHOXY-4-AMINO-5CHLOROBENZAMIDE - Google Patents
PROCESS FOR THE PREPARATION OF N (DIATHYLAMINOAETHYL) -2-METHOXY-4-AMINO-5CHLOROBENZAMIDEInfo
- Publication number
- DE2409388A1 DE2409388A1 DE19742409388 DE2409388A DE2409388A1 DE 2409388 A1 DE2409388 A1 DE 2409388A1 DE 19742409388 DE19742409388 DE 19742409388 DE 2409388 A DE2409388 A DE 2409388A DE 2409388 A1 DE2409388 A1 DE 2409388A1
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- formula
- chloride
- amino
- 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 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- GOXCIWMHHSVOKW-UHFFFAOYSA-N 4-acetamido-5-chloro-2-methoxybenzoic acid Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1C(O)=O GOXCIWMHHSVOKW-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 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 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 150000001875 compounds 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
- JSYRZFVPILRZHG-UHFFFAOYSA-M triphenyl(trichloromethyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(Cl)(Cl)Cl)C1=CC=CC=C1 JSYRZFVPILRZHG-UHFFFAOYSA-M 0.000 claims description 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 150000007522 mineralic acids Chemical class 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5463—Compounds of the type "quasi-phosphonium", e.g. (C)a-P-(Y)b wherein a+b=4, b>=1 and Y=heteroatom, generally N or O
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Societe d1Etudes Scientifiques et Industrielles de 1·Ile-de-France, S.A., Paris 7°, FrankreichSociete d 1 Etudes Scientifiques et Industrielles de 1 Ile-de-France, SA, Paris 7 °, France
"Verfahren zur Herstellung, von N-(Diäthylaminoäthyl)-2-methoxy-4-amino-5-chlorbenzamidM "Process for the preparation of N- (diethylaminoethyl) -2-methoxy-4-amino-5-chlorobenzamide M
Die Erfindung betrifft ein neues Verfahren zur Herstellung von N-(Diäthylaminoäthyl)-2-methoxy-4-amino-5-chlorbenzamid der Formel IIIThe invention relates to a new method for the production of N- (diethylaminoethyl) -2-methoxy-4-amino-5-chlorobenzamide of the formula III
CONHCH2CH2NCONHCH 2 CH 2 N
OCH.OCH.
C2H5 C 2 H 5
(III)(III)
βeinen pharmakologisch verträglichen Säureadditionssalzmmit anorganischen oder organischen Säuren, sowie seinen quartären Ammoniumsalzen, die durch Umsetzung des Benzamide der Formel III mit einen) aliphatischen oder aromatischen Alkyl!erungsmittel erhaltenβa pharmacologically acceptable acid addition salt with inorganic ones or organic acids, as well as its quaternary ammonium salts, obtained by reacting the benzamide of the formula III with an aliphatic or aromatic alkylating agent
werden.will.
409835/1057409835/1057
Sas Verfahren der Erfindung ißt dadurch gekennzeichnet, daß man Triph,enylphosphin, (C6Hc)^P, mit Tetrachlorkohlenstoff unter Bildung des Triphenyltrichlormethylphosphoniumchlorids, (C6H5),P+CCl-(Cl)",umsetzt, diese Verbindung mit 2-Methoxy-4-acetamino-5-chlorbenzoesäure unter Bildung des Tripbaaylacyloxyphosphoniumchlorids der Formel 1The process of the invention is characterized in that triph, enylphosphine, (C 6 Hc) ^ P, is reacted with carbon tetrachloride to form the triphenyltrichloromethylphosphonium chloride, (C 6 H 5 ), P + CCl- (Cl) ", this compound with 2-Methoxy-4-acetamino-5-chlorobenzoic acid with formation of the tripbaaylacyloxyphosphonium chloride of the formula 1
(D(D
NHCOCH5 NHCOCH 5
umsetzt, das sich unter Bildung des Triphenylphosphinoxide, PO(CgH1-),, in das entsprechende Säurechlorid der Formel IIconverts, which forms the triphenylphosphine oxide, PO (CgH 1 -) ,, in the corresponding acid chloride of the formula II
I-I-
OClOCl
OCH, (I1> OCH, (I1 >
NHCOCH,NHCOCH,
umwandelt,und dieses Benzoylchlorid der Formel II anschließend mit Ν,Ν-Diäthylarainoäthylamin unter Bildung des Benzamide der Formel III umsetzt.converts, and then this benzoyl chloride of the formula II with Ν, Ν-diethylarainoäthylamin with formation of the benzamides of Formula III implements.
Die Reaktion verläuft nach folgendem Schema:The reaction proceeds according to the following scheme:
409835/ 1057409835/1057
P ♦ CP ♦ C
COOHCOOH
NHCOCH.NHCOCH.
NHCOCHNHCOCH
3 , 3 ,
P+C Cl5 (Cl")P + C Cl 5 (Cl ")
Cl5(Cl")-Cl 5 (Cl ") -
ClCl
OCH,OCH,
NHCOCH,NHCOCH,
COClCOCl
ί^^ϊ—OCH·ί ^^ ϊ — OCH ·
Ij 5 Ij 5
(I)(I)
!COCH5 ! COCH 5
(ID(ID
COClCOCl
ClCl
OCH,OCH,
NHCOCH.NHCOCH.
OCH.OCH.
C8H5 C 8 H 5
(II)(II)
NH,NH,
(III)(III)
Das erfindungsgemäß hergestellte Benzamid besitzt interessante pharmakologische Eigenschaften, die in der PR-PS 1525 M/61 beschrieben sind.The benzamide produced according to the invention has interesting properties pharmacological properties described in PR-PS 1525 M / 61.
Die a,ls Ausgangsverbindung verwendete 2-Methoxy-4-acetamido-5-chlo?benzoesäure ist in der GB-PS 1 136333 sowie der US-PS 3 349 826 beschrieben.The 2-methoxy-4-acetamido-5-chlorobenzoic acid used as the starting compound is described in GB-PS 1,136,333 and in US-PS 3,349,826.
409835/1 (J B7409835/1 (J B7
Sas Beispiel beechreibt di© Erfindung, ohne in irgend einer Weise eine Beschränkung zu bedeuten·The example describes the invention without in any way to mean a limitation
Ein 500 ml fassender, mit Rührer, Kühler und Thermometer ausgerüsteter Kolben wird mit 180 ml Dioxan, 60 ml Tetrachlorkohlenstoff und 15,8 g (0,06 Mol) Triphenylphosphin beschickt. Nach 1-stündigem Erhitzen auf 700C und anschließendem Abkühlen auf etwa 5 bis 100C werden 7,3 g (0,03 Mol) 2-Methoxy-4-acetamida-5-chlorbenzoesäure zugesetzt. Die Säure ist nach 0,5-stündigenj Rühren bei dieser Temperatur praktisch völlig gelöst. Dann werden 21 g (0,18 Mol) Ν,Ν-Diäthylaminoäthylamin zugesetzt. Nach 1-stündigem Erhitzen auf 700C und anschließendem Abkühlen werden die Lösungsmittel unter vermindertem Druck abgedampft und der Rückstand in Wasser eingegossen. Anschließend wird mit konzentrierter Chlorwasserstoffsäure biB zur sauren Reaktion versetzt und der Niederschlag abfiltriert. # A 500 ml flask equipped with a stirrer, condenser and thermometer is charged with 180 ml of dioxane, 60 ml of carbon tetrachloride and 15.8 g (0.06 mol) of triphenylphosphine. After 1 hour of heating to 70 ° C. and subsequent cooling to about 5 to 10 ° C., 7.3 g (0.03 mol) of 2-methoxy-4-acetamida-5-chlorobenzoic acid are added. The acid is practically completely dissolved after stirring for 0.5 hours at this temperature. Then 21 g (0.18 mol) of Ν, Ν-diethylaminoethylamine are added. After heating to 70 ° C. for 1 hour and subsequent cooling, the solvents are evaporated off under reduced pressure and the residue is poured into water. Concentrated hydrochloric acid is then added to an acidic reaction and the precipitate is filtered off. #
Das Filtrat wird mit Natronlauge oder Soda bis zum pH 10 versetzt.und anschließend abfiltriert· Der kristalline Niederschlag wird während 0,5 Stunden unter Sieden mit 5n NaOH oder Soda umgesetzt, anschließend wird das Reaktionsgemisch abgekühlt, filtriert und im Trockenschrank bei 500C getrocknet.The filtrate is treated with caustic soda or soda ash to pH 10 versetzt.und then filtered · The crystalline precipitate is reacted for 0.5 hours under boiling with 5N NaOH or soda, then the reaction mixture is cooled, filtered and dried in a drying oven at 50 0 C dried .
Nach dem Umkristallisieren.aus Benzol erhält man 2,9 g (33 Prozent Ausbeute ) N- ( Diäthylaainöäthyl) ^-methoxy^-amino-S-chlorbenzamid vom P. 1430C,After recrystallization from benzene, 2.9 g (33 percent yield) of N- (diethylaainoethyl) ^ -methoxy ^ -amino-S-chlorobenzamide from P. 143 0 C,
A09836/10b7A09836 / 10b7
Claims (1)
umsetzt,KMCCCH,
implements,
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7307240A FR2219151B1 (en) | 1973-02-28 | 1973-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2409388A1 true DE2409388A1 (en) | 1974-08-29 |
Family
ID=9115596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742409388 Pending DE2409388A1 (en) | 1973-02-28 | 1974-02-27 | PROCESS FOR THE PREPARATION OF N (DIATHYLAMINOAETHYL) -2-METHOXY-4-AMINO-5CHLOROBENZAMIDE |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS49134646A (en) |
| AR (1) | AR203279A1 (en) |
| AT (1) | AT341503B (en) |
| CA (1) | CA1026375A (en) |
| DE (1) | DE2409388A1 (en) |
| ES (1) | ES423568A1 (en) |
| FR (1) | FR2219151B1 (en) |
| GB (1) | GB1420897A (en) |
| IE (1) | IE38927B1 (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR88808E (en) * | 1964-06-09 | 1967-06-15 |
-
1973
- 1973-02-28 FR FR7307240A patent/FR2219151B1/fr not_active Expired
-
1974
- 1974-02-23 ES ES423568A patent/ES423568A1/en not_active Expired
- 1974-02-25 JP JP2223674A patent/JPS49134646A/ja active Pending
- 1974-02-25 CA CA193,453A patent/CA1026375A/en not_active Expired
- 1974-02-26 GB GB866774A patent/GB1420897A/en not_active Expired
- 1974-02-26 IE IE38874A patent/IE38927B1/en unknown
- 1974-02-27 DE DE19742409388 patent/DE2409388A1/en active Pending
- 1974-02-27 AR AR25251874A patent/AR203279A1/en active
- 1974-02-27 AT AT159374A patent/AT341503B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AR203279A1 (en) | 1975-08-29 |
| ES423568A1 (en) | 1976-05-16 |
| GB1420897A (en) | 1976-01-14 |
| FR2219151A1 (en) | 1974-09-20 |
| FR2219151B1 (en) | 1977-12-30 |
| ATA159374A (en) | 1977-06-15 |
| IE38927L (en) | 1974-08-28 |
| AT341503B (en) | 1978-02-10 |
| JPS49134646A (en) | 1974-12-25 |
| IE38927B1 (en) | 1978-07-05 |
| CA1026375A (en) | 1978-02-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |