ES423630A1 - Production of 2,5-disubstituted benzamides - Google Patents
Production of 2,5-disubstituted benzamidesInfo
- Publication number
- ES423630A1 ES423630A1 ES423630A ES423630A ES423630A1 ES 423630 A1 ES423630 A1 ES 423630A1 ES 423630 A ES423630 A ES 423630A ES 423630 A ES423630 A ES 423630A ES 423630 A1 ES423630 A1 ES 423630A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- radical
- molecular weight
- alcoholic
- low molecular
- 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
- 229940054066 benzamide antipsychotics Drugs 0.000 title abstract 2
- 150000003936 benzamides Chemical class 0.000 title abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 230000001476 alcoholic effect Effects 0.000 abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- 125000003158 alcohol group Chemical group 0.000 abstract 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000002632 imidazolidinyl group Chemical group 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- -1 morpholino, thiazolidinyl Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 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 abstract 1
- 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 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D227/00—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00
- C07D227/02—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D227/04—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms
-
- 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
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)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Preparation procedure for benzamides of general formula: ** (See formula) ** as well as its addition salts with pharmaceutically acceptable mineral or organic acids and its quaternary ammonium salts; formula (I) in which A can be either a low molecular weight monoalkoxylamino or dialcoylamino radical in which the alcohol groups can be joined together to form a ring with or without nitrogen, oxygen or sulfur, and when the ring contains an atom nitrogen, the nitrogen atom can be attached to a low molecular weight alcohol group, the rings being thus formed, for example: pyrrolidinyl, piperidinyl, imidazolidinyl, piperazine, morpholino, thiazolidinyl, or A can be a heterocyclic radical of the shape: ** (See formula) ** R being a low molecular weight alcoholic radical, or alcoholic; m is an integer less than 4; B can be a low molecular weight alcohol radical or an alcohol radical; n = 1 or 2; I can be an amino, mon-alkoxylamino or dialcohilamino, alcoholic or alcoholic radical, said process consisting of starting from triphenylphosphine (C6H5) 3P, treating it with carbon tetrachloride so as to obtain triphenyltrichloromethylphosphonium chloride: (C6H5) P + C Cl3 (Cl) - and react this compound with a disubstituted benzoic acid in positions 2 and 5, of the formula: ** (See formula) ** where B and X have the same meanings as mentioned above, thus obtaining a triarylacyloxyphosphonium chloride of the formula: ** (See formula) ** which is transformed into the corresponding acid chloride: ** (See formula) ** with triphenylphosphine oxide formation: PO (C6H5) 3 and then this benzoyl chloride (IV) disubstituted in positions 2 and 5 is reacted with an amine of formula: H2N (CH2) nA (V) where A has the same value as previously described, so that the desired benzamide of formula I is obtained. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7307645A FR2219942B1 (en) | 1973-03-02 | 1973-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES423630A1 true ES423630A1 (en) | 1976-05-01 |
Family
ID=9115740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES423630A Expired ES423630A1 (en) | 1973-03-02 | 1974-02-26 | Production of 2,5-disubstituted benzamides |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5726509B2 (en) |
| AR (1) | AR202295A1 (en) |
| AT (1) | AT331222B (en) |
| CA (1) | CA1015364A (en) |
| DE (1) | DE2409387A1 (en) |
| ES (1) | ES423630A1 (en) |
| FR (1) | FR2219942B1 (en) |
| GB (1) | GB1420896A (en) |
| IE (1) | IE38930B1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2305176A1 (en) * | 1975-03-28 | 1976-10-22 | Ile De France | NEW DRUG BASED ON N- (DIETHYLAMINOETHYL) 2-METHOXY-5-METHYL-SULFONYL BENZAMIDE |
| JPS6329764Y2 (en) * | 1980-12-15 | 1988-08-10 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB994023A (en) * | 1961-07-25 | 1965-06-02 | Ile De France | Substituted n-(tertiary amino alkyl)benzamides |
-
1973
- 1973-03-02 FR FR7307645A patent/FR2219942B1/fr not_active Expired
-
1974
- 1974-02-25 JP JP2223874A patent/JPS5726509B2/ja not_active Expired
- 1974-02-25 CA CA193,355A patent/CA1015364A/en not_active Expired
- 1974-02-26 GB GB860074A patent/GB1420896A/en not_active Expired
- 1974-02-26 IE IE39174A patent/IE38930B1/en unknown
- 1974-02-26 ES ES423630A patent/ES423630A1/en not_active Expired
- 1974-02-27 AR AR25252374A patent/AR202295A1/en active
- 1974-02-27 DE DE19742409387 patent/DE2409387A1/en active Pending
- 1974-02-27 AT AT159174A patent/AT331222B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1420896A (en) | 1976-01-14 |
| CA1015364A (en) | 1977-08-09 |
| FR2219942A1 (en) | 1974-09-27 |
| ATA159174A (en) | 1975-11-15 |
| AT331222B (en) | 1976-08-10 |
| AR202295A1 (en) | 1975-05-30 |
| IE38930L (en) | 1974-09-02 |
| IE38930B1 (en) | 1978-07-05 |
| DE2409387A1 (en) | 1974-09-05 |
| FR2219942B1 (en) | 1977-12-30 |
| JPS5726509B2 (en) | 1982-06-04 |
| JPS49134651A (en) | 1974-12-25 |
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