DE2444763A1 - Verfahren zur herstellung von 2,5disubstituierten benzamiden - Google Patents
Verfahren zur herstellung von 2,5disubstituierten benzamidenInfo
- Publication number
- DE2444763A1 DE2444763A1 DE19742444763 DE2444763A DE2444763A1 DE 2444763 A1 DE2444763 A1 DE 2444763A1 DE 19742444763 DE19742444763 DE 19742444763 DE 2444763 A DE2444763 A DE 2444763A DE 2444763 A1 DE2444763 A1 DE 2444763A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- molecular weight
- low molecular
- preparation
- general formula
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 5
- 229940054066 benzamide antipsychotics Drugs 0.000 title description 2
- 150000003936 benzamides Chemical class 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
- -1 l'iperazino Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 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
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AHYZXIUNHHXCHO-UHFFFAOYSA-N 2-ethylsulfonylbenzoic acid Chemical compound CCS(=O)(=O)C1=CC=CC=C1C(O)=O AHYZXIUNHHXCHO-UHFFFAOYSA-N 0.000 description 1
- USSHTWOXWQEPPI-UHFFFAOYSA-N 6-sulfonylcyclohexa-2,4-diene-1-carboxylic acid Chemical compound OC(=O)C1C=CC=CC1=S(=O)=O USSHTWOXWQEPPI-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-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
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000002706 hydrostatic effect Effects 0.000 description 1
- 239000007788 liquid Substances 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
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 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
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7335601A FR2246545B1 (enExample) | 1973-10-04 | 1973-10-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2444763A1 true DE2444763A1 (de) | 1975-04-10 |
Family
ID=9125956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742444763 Withdrawn DE2444763A1 (de) | 1973-10-04 | 1974-09-19 | Verfahren zur herstellung von 2,5disubstituierten benzamiden |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5721198B2 (enExample) |
| AR (1) | AR205547A1 (enExample) |
| AT (1) | AT338236B (enExample) |
| CA (1) | CA1022941A (enExample) |
| DE (1) | DE2444763A1 (enExample) |
| ES (1) | ES430656A1 (enExample) |
| FI (1) | FI285174A7 (enExample) |
| FR (1) | FR2246545B1 (enExample) |
| GB (1) | GB1445257A (enExample) |
| IE (1) | IE39925B1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2478093A1 (fr) * | 1980-03-12 | 1981-09-18 | Ile De France | Nouveau procede de preparation de n-(1-alkyl (ou allyl) 2-pyrrolidinyl-methyl)2-methoxy (ou 2,3-dimethoxy) 5-sulfamoyl (ou sulfamoyl substitue) |
| US5136082A (en) * | 1990-08-03 | 1992-08-04 | Himont Incorporated | Process for preparing organic esters and amides and catalyst system therefor |
| DE60135457D1 (de) | 2000-05-29 | 2008-10-02 | Chugai Pharmaceutical Co Ltd | Verfahren zur herstellung von stickstoffverbindungen |
-
1973
- 1973-10-04 FR FR7335601A patent/FR2246545B1/fr not_active Expired
-
1974
- 1974-01-01 AR AR255857A patent/AR205547A1/es active
- 1974-09-19 DE DE19742444763 patent/DE2444763A1/de not_active Withdrawn
- 1974-09-30 JP JP11323074A patent/JPS5721198B2/ja not_active Expired
- 1974-09-30 CA CA210,297A patent/CA1022941A/en not_active Expired
- 1974-09-30 GB GB4227874A patent/GB1445257A/en not_active Expired
- 1974-09-30 FI FI2851/74A patent/FI285174A7/fi unknown
- 1974-10-01 AT AT787074A patent/AT338236B/de not_active IP Right Cessation
- 1974-10-01 IE IE2034/74A patent/IE39925B1/xx unknown
- 1974-10-03 ES ES0430656A patent/ES430656A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AR205547A1 (es) | 1976-05-14 |
| GB1445257A (en) | 1976-08-11 |
| CA1022941A (en) | 1977-12-20 |
| IE39925L (en) | 1975-04-04 |
| IE39925B1 (en) | 1979-01-31 |
| ES430656A1 (es) | 1976-11-16 |
| JPS5062949A (enExample) | 1975-05-29 |
| FR2246545A1 (enExample) | 1975-05-02 |
| AT338236B (de) | 1977-08-10 |
| ATA787074A (de) | 1976-12-15 |
| FI285174A7 (enExample) | 1975-04-05 |
| FR2246545B1 (enExample) | 1978-09-15 |
| JPS5721198B2 (enExample) | 1982-05-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |