RU2007125710A - Способ получения n-фенилпиразол-1-карбоксамидов - Google Patents
Способ получения n-фенилпиразол-1-карбоксамидов Download PDFInfo
- Publication number
- RU2007125710A RU2007125710A RU2007125710/04A RU2007125710A RU2007125710A RU 2007125710 A RU2007125710 A RU 2007125710A RU 2007125710/04 A RU2007125710/04 A RU 2007125710/04A RU 2007125710 A RU2007125710 A RU 2007125710A RU 2007125710 A RU2007125710 A RU 2007125710A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- sulfonyl chloride
- alkyl
- combined
- compounds
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- UQMSSNPGHUMLNM-UHFFFAOYSA-N n-phenylpyrazole-1-carboxamide Chemical class C1=CC=NN1C(=O)NC1=CC=CC=C1 UQMSSNPGHUMLNM-UHFFFAOYSA-N 0.000 title 1
- 229910052801 chlorine Inorganic materials 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 7
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical group CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims 1
- 150000001448 anilines Chemical class 0.000 claims 1
- -1 carboxylic acid compound Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- QARBMVPHQWIHKH-KHWXYDKHSA-N methanesulfonyl chloride Chemical group C[35S](Cl)(=O)=O QARBMVPHQWIHKH-KHWXYDKHSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 150000003512 tertiary amines Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- 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)
Claims (12)
1. Способ получения соединения формулы 1
где R1 представляет CH3 или Cl;
R2 представляет Br, Cl, I или CN;
R3 представляет H или C1-C4 алкил;
R4 представляет Cl, Br, CF3, OCF2H или OCH2CF3;
R5 представляет F, Cl или Br;
R6 представляет Н, F или Cl;
Z представляет CR7 или N и
R7 представляет Н, F, Cl или Br, включающий
объединение (1) соединения карбоновой кислоты формулы 2
(2) соединения анилина формулы 3
и (3) сульфонилхлорида, с образованием соединения формулы 1.
2. Способ по п.1, где сульфонилхлорид представлен формулой 4
R8S(O)2Cl
где R8 представляет C1-C4 алкил, C1-C2 галогеналкил или фенил, необязательно замещенные 1-3 заместителями, выбранными из группы, состоящей из галогена, C1-C3 алкила и нитро.
3. Способ по п.2, где сульфонилхлоридом является метансульфонилхлорид.
4. Способ по п.1, где карбоновую кислоту формулы 2 объединяют с анилином формулы 3 для получения смеси и затем смесь объединяют с сульфонилхлоридом.
5. Способ по п.4, где основание объединяют с соединениями формул 2 и 3, чтобы получить смесь перед объединением с сульфонилхлоридом.
6. Способ по п.5, где основание выбрано из третичных аминов.
7. Способ по п.6, где основание выбрано из, необязательно, замещенных пиридинов.
8. Способ по п.7, где основание выбрано из 2-пиколина, 3-пиколина, 2,6-лутидина и пиридина.
9. Способ по п.8, где сульфонилхлорид представлен формулой 4
R8S(O)2Cl
где R8 представляет C1-C4 алкил, C1-C2 галогеналкил или фенил, необязательно замещенные 1-3 заместителями, выбранными из группы, состоящей из галогена, C1-C3 алкила и нитро.
10. Способ по п.1 или 4, где растворитель объединяют с соединениями формул 2 и 3 и сульфонилхлоридом.
11. Способ по п.10, где растворителем является ацетонитрил.
12. Соединение формулы 3
где R1 представляет CH3 или Cl;
R2 представляет Br, Cl, I или CN и
R3 представляет H или C1-C4 алкил;
при условии, что
(а) когда R1 и R2 представляют Cl, тогда R3 не является Н, CH2CH3 или CH(CH3)CH2CH3;
(b) когда R1 представляет CH3 и R2 представляет Cl, Br или CN, тогда R3 не является CH3 или CH(CH3)2;
(с) когда R1 представляет Cl и R2 представляет Cl или Br, тогда R3 не является CH3 или CH(CH3)2; и
(d) когда R1 представляет CH3 и R2 представляет CN, тогда R3 не является H.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63389904P | 2004-12-07 | 2004-12-07 | |
| US60/633,899 | 2004-12-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2007125710A true RU2007125710A (ru) | 2009-01-20 |
| RU2397165C2 RU2397165C2 (ru) | 2010-08-20 |
Family
ID=36353328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007125710/04A RU2397165C2 (ru) | 2004-12-07 | 2005-12-06 | Способ получения n-фенилпиразол-1-карбоксамидов |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7528260B2 (ru) |
| EP (1) | EP1828164B1 (ru) |
| JP (1) | JP4996477B2 (ru) |
| KR (1) | KR101280086B1 (ru) |
| CN (2) | CN101072767B (ru) |
| AR (1) | AR051839A1 (ru) |
| AT (1) | ATE408609T1 (ru) |
| AU (1) | AU2005314155B2 (ru) |
| BR (1) | BRPI0516911B1 (ru) |
| CA (1) | CA2587528C (ru) |
| DE (1) | DE602005009866D1 (ru) |
| DK (1) | DK1828164T3 (ru) |
| ES (1) | ES2314753T3 (ru) |
| GT (1) | GT200500354A (ru) |
| IL (1) | IL183091A (ru) |
| MX (1) | MX265618B (ru) |
| PL (1) | PL1828164T3 (ru) |
| RS (1) | RS50672B (ru) |
| RU (1) | RU2397165C2 (ru) |
| TW (1) | TWI363756B (ru) |
| UA (1) | UA93861C2 (ru) |
| WO (1) | WO2006062978A1 (ru) |
| ZA (1) | ZA200704202B (ru) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2689126C2 (ru) * | 2014-05-29 | 2019-05-24 | ЭфЭмСи Корпорейшн | Способ получения 3-метил-2-нитробензойной кислоты посредством окисления воздухом |
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| RU2443679C2 (ru) | 2006-07-19 | 2012-02-27 | Е.И.Дюпон Де Немур Энд Компани | Способ получения 3-замещенных 2-амино-5-галогенбензамидов |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| RU2689126C2 (ru) * | 2014-05-29 | 2019-05-24 | ЭфЭмСи Корпорейшн | Способ получения 3-метил-2-нитробензойной кислоты посредством окисления воздухом |
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