CN1149202C - 制备4-氨基-1，2，4-三唑啉-5-酮的改进方法 - Google Patents
制备4-氨基-1，2，4-三唑啉-5-酮的改进方法 Download PDFInfo
- Publication number
- CN1149202C CN1149202C CNB991159977A CN99115997A CN1149202C CN 1149202 C CN1149202 C CN 1149202C CN B991159977 A CNB991159977 A CN B991159977A CN 99115997 A CN99115997 A CN 99115997A CN 1149202 C CN1149202 C CN 1149202C
- Authority
- CN
- China
- Prior art keywords
- ketone
- amino
- hydrazine hydrate
- toluene
- mol ratio
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- NADWTGWNQJDBQR-UHFFFAOYSA-N 4-amino-3h-1,2,4-triazol-5-one Chemical compound NN1CN=NC1=O NADWTGWNQJDBQR-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 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 claims abstract description 16
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims abstract description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- -1 oxadiazole quinoline ketone Chemical class 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 230000005540 biological transmission Effects 0.000 claims 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims 2
- 238000001556 precipitation Methods 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- FMCUPJKTGNBGEC-UHFFFAOYSA-N 1,2,4-triazol-4-amine Chemical compound NN1C=NN=C1 FMCUPJKTGNBGEC-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 229910052728 basic metal Inorganic materials 0.000 claims 1
- 150000003818 basic metals Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 abstract description 14
- 150000007514 bases Chemical class 0.000 abstract description 12
- SZKVXFRLGVPSNA-UHFFFAOYSA-N 1-amino-4h-triazol-5-one Chemical class NN1N=NCC1=O SZKVXFRLGVPSNA-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 14
- 238000004821 distillation Methods 0.000 description 5
- 239000013505 freshwater Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003002 pH adjusting agent Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- WNWOTMKHOLCHRJ-UHFFFAOYSA-N 1,4-dihydrotriazol-5-one Chemical compound O=C1CN=NN1 WNWOTMKHOLCHRJ-UHFFFAOYSA-N 0.000 description 1
- MZTLRWDZUSEEME-UHFFFAOYSA-N 3-amino-4H-triazol-5-one Chemical compound NN1CC(=O)N=N1 MZTLRWDZUSEEME-UHFFFAOYSA-N 0.000 description 1
- CVAZHHVXKJQSCH-UHFFFAOYSA-N 5-propan-2-yloxadiazol-4-one Chemical compound CC(C)C1ON=NC1=O CVAZHHVXKJQSCH-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960005437 etoperidone Drugs 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 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
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/210321 | 1998-12-11 | ||
| US09/210,321 US5912354A (en) | 1998-12-11 | 1998-12-11 | Process for preparing 4-amino-1,2,4-triazolin-5-ones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1263888A CN1263888A (zh) | 2000-08-23 |
| CN1149202C true CN1149202C (zh) | 2004-05-12 |
Family
ID=22782436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB991159977A Expired - Lifetime CN1149202C (zh) | 1998-12-11 | 1999-12-11 | 制备4-氨基-1，2，4-三唑啉-5-酮的改进方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5912354A (OSRAM) |
| EP (1) | EP1018509B1 (OSRAM) |
| JP (1) | JP4700777B2 (OSRAM) |
| CN (1) | CN1149202C (OSRAM) |
| AT (1) | ATE240302T1 (OSRAM) |
| BR (1) | BR9907483B1 (OSRAM) |
| CA (1) | CA2291508A1 (OSRAM) |
| DE (1) | DE69907857T2 (OSRAM) |
| DK (1) | DK1018509T3 (OSRAM) |
| IL (1) | IL133375A (OSRAM) |
| IN (1) | IN186590B (OSRAM) |
| ZA (1) | ZA997593B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6197971B1 (en) | 1999-12-27 | 2001-03-06 | Bayer Corporation | Process for the manufacture of substituted triazolinones |
| PT2688885T (pt) * | 2011-03-22 | 2016-09-06 | Bayer Ip Gmbh | Amidas de ácido n-(1,3,4-oxadiazol-2-il)-arilcarboxílico e a utilização das mesmas como herbicidas |
| KR101273895B1 (ko) * | 2011-07-28 | 2013-06-17 | 케이에스랩(주) | 아미노-트리아졸리논의 제조방법 |
| CN111808035B (zh) * | 2020-07-10 | 2022-06-24 | 北京怡力生物科技有限公司 | 一种4-氨基-3-异丙基-1,2,4-三唑啉-5-酮的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3934081A1 (de) * | 1989-10-12 | 1991-04-18 | Bayer Ag | Sulfonylaminocarbonyltriazolinone |
| FR2618779B1 (fr) * | 1987-07-31 | 1991-01-04 | Poudres & Explosifs Ste Nale | Nouveau procede de preparation des 1,2,4-triazol-3-ones |
| DE3827264A1 (de) * | 1987-12-22 | 1989-07-13 | Bayer Ag | Verfahren zur herstellung von 4-amino-1,2,4-triazol-5-onen |
| DE19530450A1 (de) * | 1995-08-18 | 1997-02-20 | Bayer Ag | Verfahren zur Herstellung von substituierten Aminotriazolinonen |
-
1998
- 1998-12-11 US US09/210,321 patent/US5912354A/en not_active Expired - Lifetime
-
1999
- 1999-11-24 IN IN840BO1999 patent/IN186590B/en unknown
- 1999-12-02 AT AT99123927T patent/ATE240302T1/de not_active IP Right Cessation
- 1999-12-02 EP EP99123927A patent/EP1018509B1/en not_active Expired - Lifetime
- 1999-12-02 DK DK99123927T patent/DK1018509T3/da active
- 1999-12-02 DE DE69907857T patent/DE69907857T2/de not_active Expired - Lifetime
- 1999-12-03 CA CA002291508A patent/CA2291508A1/en not_active Abandoned
- 1999-12-07 JP JP34737699A patent/JP4700777B2/ja not_active Expired - Lifetime
- 1999-12-08 IL IL13337599A patent/IL133375A/en not_active IP Right Cessation
- 1999-12-10 ZA ZA9907593A patent/ZA997593B/xx unknown
- 1999-12-11 CN CNB991159977A patent/CN1149202C/zh not_active Expired - Lifetime
- 1999-12-13 BR BRPI9907483-4A patent/BR9907483B1/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BR9907483A (pt) | 2001-07-17 |
| ATE240302T1 (de) | 2003-05-15 |
| US5912354A (en) | 1999-06-15 |
| BR9907483B1 (pt) | 2010-07-13 |
| DE69907857D1 (de) | 2003-06-18 |
| ZA997593B (en) | 2000-06-12 |
| IL133375A0 (en) | 2001-04-30 |
| CN1263888A (zh) | 2000-08-23 |
| DE69907857T2 (de) | 2004-03-11 |
| EP1018509B1 (en) | 2003-05-14 |
| IN186590B (OSRAM) | 2001-10-06 |
| JP4700777B2 (ja) | 2011-06-15 |
| JP2000178262A (ja) | 2000-06-27 |
| EP1018509A1 (en) | 2000-07-12 |
| IL133375A (en) | 2004-07-25 |
| DK1018509T3 (da) | 2003-08-25 |
| CA2291508A1 (en) | 2000-06-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: WD Ref document number: 1028037 Country of ref document: HK |
|
| TR01 | Transfer of patent right |
Effective date of registration: 20170713 Address after: American Pennsylvania Co-patentee after: Bayer Pharma Aktiengesellschaft Patentee after: Miles Inc. Address before: American Pennsylvania Co-patentee before: Bayer Aktiengesellschaft Patentee before: Miles Inc. |
|
| TR01 | Transfer of patent right | ||
| CX01 | Expiry of patent term |
Granted publication date: 20040512 |
|
| CX01 | Expiry of patent term |