CN1064678C - 4－氨基－1,2,4－三唑的制备方法 - Google Patents
4－氨基－1,2,4－三唑的制备方法 Download PDFInfo
- Publication number
- CN1064678C CN1064678C CN97126383A CN97126383A CN1064678C CN 1064678 C CN1064678 C CN 1064678C CN 97126383 A CN97126383 A CN 97126383A CN 97126383 A CN97126383 A CN 97126383A CN 1064678 C CN1064678 C CN 1064678C
- Authority
- CN
- China
- Prior art keywords
- hydrazine
- triazole
- amino
- product
- reaction
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title abstract description 5
- FMCUPJKTGNBGEC-UHFFFAOYSA-N 1,2,4-triazol-4-amine Chemical compound NN1C=NN=C1 FMCUPJKTGNBGEC-UHFFFAOYSA-N 0.000 title abstract description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 3
- 238000010790 dilution Methods 0.000 claims abstract description 3
- 239000012895 dilution Substances 0.000 claims abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 8
- 238000001953 recrystallisation Methods 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000007812 deficiency Effects 0.000 abstract description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- POVXOWVFLAAVBH-UHFFFAOYSA-N n-formamidoformamide Chemical compound O=CNNC=O POVXOWVFLAAVBH-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR13590/1996 | 1996-11-07 | ||
| FR13590/96 | 1996-11-07 | ||
| FR9613590 | 1996-11-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1190655A CN1190655A (zh) | 1998-08-19 |
| CN1064678C true CN1064678C (zh) | 2001-04-18 |
Family
ID=9497419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97126383A Expired - Fee Related CN1064678C (zh) | 1996-11-07 | 1997-11-07 | 4－氨基－1,2,4－三唑的制备方法 |
Country Status (15)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7745635B1 (en) * | 2003-06-16 | 2010-06-29 | Drake Greg W | Energetic ionic salts |
| US7045635B2 (en) * | 2004-01-27 | 2006-05-16 | Bwxt Pantex, Llc | Process for the synthesis of 4-amino-4H-1,2,4-triazole |
| FR2875804A1 (fr) * | 2004-09-27 | 2006-03-31 | Arkema Sa | Procede de preparation du 4-amino-1,2,4 triazole |
| WO2012146598A1 (en) | 2011-04-28 | 2012-11-01 | Basf Se | Process for the preparation of 2-substituted 4-amino-2,4-dihydro-[1,2,4]triazole-3-thiones |
| US20140275559A1 (en) * | 2013-03-13 | 2014-09-18 | Dow Agrosciences Llc | Preparation of certain (substituted-phenyl)-triazolyl-(substituted phenyl) molecules, and intermediates and insecticides related thereto |
| WO2014158638A1 (en) * | 2013-03-13 | 2014-10-02 | Dow Agrosciences Llc | Preparation of certain (substituted phenyl)-triazolyl-(substituted phenyl) molecules, and intermediates and insecticides related thereto |
| RU2739325C1 (ru) * | 2020-03-20 | 2020-12-22 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Российский химико-технологический университет имени Д.И. Менделеева" (РХТУ им. Д.И. Менделеева) | Способ получения 4-амино-1,2,4-триазола |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0269308A2 (en) * | 1986-11-24 | 1988-06-01 | Reilly Industries, Inc. | Process for the synthesis of 4-amino-1,2,4-(4H)triazole derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5099028A (en) * | 1986-11-24 | 1992-03-24 | Reilly Tar And Chemical Corporation | Process for the synthesis of 4-amino-1,2,4-(4h)triazole derivatives |
| JPH04308582A (ja) | 1991-04-04 | 1992-10-30 | Ishihara Sangyo Kaisha Ltd | ４−アミノ−１，２，４−トリアゾールの製法 |
| RU2036912C1 (ru) * | 1992-08-05 | 1995-06-09 | Научно-внедренческое предприятие "Ноосфера - центр" | Способ получения 4-амино-1,2,4-триазола |
-
1997
- 1997-10-24 AT AT97402531T patent/ATE203525T1/de not_active IP Right Cessation
- 1997-10-24 PT PT97402531T patent/PT841328E/pt unknown
- 1997-10-24 DE DE69705802T patent/DE69705802T2/de not_active Expired - Fee Related
- 1997-10-24 ES ES97402531T patent/ES2160909T3/es not_active Expired - Lifetime
- 1997-10-24 DK DK97402531T patent/DK0841328T3/da active
- 1997-10-24 EP EP97402531A patent/EP0841328B1/fr not_active Expired - Lifetime
- 1997-11-04 IL IL12210097A patent/IL122100A/en not_active IP Right Cessation
- 1997-11-06 CA CA002218707A patent/CA2218707C/fr not_active Expired - Fee Related
- 1997-11-06 US US08/965,144 patent/US6040456A/en not_active Expired - Fee Related
- 1997-11-06 BR BR9705433A patent/BR9705433A/pt not_active Application Discontinuation
- 1997-11-07 JP JP09322433A patent/JP3131178B2/ja not_active Expired - Fee Related
- 1997-11-07 CN CN97126383A patent/CN1064678C/zh not_active Expired - Fee Related
- 1997-11-07 IN IN3203DE1997 patent/IN187905B/en unknown
- 1997-11-07 KR KR1019970058722A patent/KR100257052B1/ko not_active Expired - Fee Related
-
1999
- 1999-09-03 US US09/390,286 patent/US6504033B1/en not_active Expired - Fee Related
-
2001
- 2001-09-20 GR GR20010401536T patent/GR3036679T3/el not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0269308A2 (en) * | 1986-11-24 | 1988-06-01 | Reilly Industries, Inc. | Process for the synthesis of 4-amino-1,2,4-(4H)triazole derivatives |
Non-Patent Citations (3)
| Title |
|---|
| CHEMICAL ABSTRACT VOL 53(10)文摘号9197G 1959.1.1 A N KOST AND F GENTS ET AL * |
| CHEMICAL ABSTRACT VOL 53(10)文摘号9197G 1959.1.1 A N KOST AND F GENTS ET AL;JORNAL OF ORGANI CHEMISTRY VOL 18 1953.7.1 ROBERT M HERBAT ET AL * |
| JORNAL OF ORGANI CHEMISTRY VOL 18 1953.7.1 ROBERT M HERBAT ET AL * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69705802D1 (de) | 2001-08-30 |
| CA2218707C (fr) | 2003-09-09 |
| EP0841328B1 (fr) | 2001-07-25 |
| BR9705433A (pt) | 1999-05-25 |
| US6040456A (en) | 2000-03-21 |
| IL122100A0 (en) | 1998-04-05 |
| ATE203525T1 (de) | 2001-08-15 |
| CA2218707A1 (fr) | 1998-05-07 |
| DK0841328T3 (da) | 2001-10-22 |
| KR19980042199A (ko) | 1998-08-17 |
| EP0841328A1 (fr) | 1998-05-13 |
| US6504033B1 (en) | 2003-01-07 |
| DE69705802T2 (de) | 2001-11-15 |
| JPH10139766A (ja) | 1998-05-26 |
| ES2160909T3 (es) | 2001-11-16 |
| GR3036679T3 (en) | 2001-12-31 |
| CN1190655A (zh) | 1998-08-19 |
| JP3131178B2 (ja) | 2001-01-31 |
| IL122100A (en) | 2002-12-01 |
| IN187905B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2002-07-20 |
| PT841328E (pt) | 2001-11-30 |
| KR100257052B1 (ko) | 2000-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C56 | Change in the name or address of the patentee |
Owner name: ATUOFEINA CORP. Free format text: FORMER NAME OR ADDRESS: ELF ATOCHEM S. A. |
|
| CP01 | Change in the name or title of a patent holder |
Patentee after: Atofina company Patentee before: Elf Atochem S.A. |
|
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |