SU577989A3 - Способ получени производных 3-окси-1,2,4-триазола - Google Patents
Способ получени производных 3-окси-1,2,4-триазолаInfo
- Publication number
- SU577989A3 SU577989A3 SU7502163216A SU2163216A SU577989A3 SU 577989 A3 SU577989 A3 SU 577989A3 SU 7502163216 A SU7502163216 A SU 7502163216A SU 2163216 A SU2163216 A SU 2163216A SU 577989 A3 SU577989 A3 SU 577989A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ethyl
- acid
- solution
- carbon atoms
- ester
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 239000002253 acid Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 125000004494 ethyl ester group Chemical group 0.000 description 10
- -1 1,5-disubstituted 3-hydroxy-1,2,4-triazole Chemical class 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- JUBQWIQZJYAKGO-UHFFFAOYSA-N 3-cyano-3-hydroxypropanoic acid Chemical compound N#CC(O)CC(O)=O JUBQWIQZJYAKGO-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- 235000012093 Myrtus ugni Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101100095854 Schizosaccharomyces pombe (strain 972 / ATCC 24843) skp1 gene Proteins 0.000 description 1
- 244000061461 Tema Species 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012707 chemical precursor Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229950007046 chlorphentermine Drugs 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- CWYKSVVUHGYPDF-UHFFFAOYSA-N ethyl n-(ethylamino)carbamate Chemical compound CCNNC(=O)OCC CWYKSVVUHGYPDF-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- IBBLRJGOOANPTQ-JKVLGAQCSA-N quinapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 IBBLRJGOOANPTQ-JKVLGAQCSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1177174A CH601266A5 (en:Method) | 1974-08-29 | 1974-08-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU577989A3 true SU577989A3 (ru) | 1977-10-25 |
Family
ID=4376715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7502163216A SU577989A3 (ru) | 1974-08-29 | 1975-08-18 | Способ получени производных 3-окси-1,2,4-триазола |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5910351B2 (en:Method) |
| AT (1) | AT342587B (en:Method) |
| AU (1) | AU499371B2 (en:Method) |
| BE (1) | BE832830A (en:Method) |
| CA (1) | CA1070696A (en:Method) |
| CH (1) | CH601266A5 (en:Method) |
| CS (1) | CS193522B2 (en:Method) |
| DD (1) | DD122535A5 (en:Method) |
| DE (1) | DE2537973A1 (en:Method) |
| ES (1) | ES440532A1 (en:Method) |
| FR (1) | FR2283132A1 (en:Method) |
| GB (1) | GB1512456A (en:Method) |
| HU (1) | HU172771B (en:Method) |
| IL (1) | IL48008A (en:Method) |
| NL (1) | NL7510012A (en:Method) |
| NZ (1) | NZ178271A (en:Method) |
| SU (1) | SU577989A3 (en:Method) |
| ZA (1) | ZA755512B (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2158734C2 (ru) * | 1994-11-21 | 2000-11-10 | Байер Аг | Производные триазолила, способ их получения и фунгицидное средство |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3070073D1 (en) * | 1979-10-22 | 1985-03-14 | Glaxo Group Ltd | 1,2,4-triazole derivatives, processes for their production and pharmaceutical compositions containing them |
| GB2064515B (en) * | 1979-10-23 | 1983-06-29 | Glaxo Group Ltd | Heterocyclic derivatives processes for their production and pharmaceutical compositions containing them |
| ES511107A0 (es) * | 1981-04-09 | 1983-02-01 | Hoechst Ag | "procedimiento para la preparacion de 3-hidroxi-1,2,4-triazoles". |
| DE3939952A1 (de) * | 1989-12-02 | 1991-06-06 | Bayer Ag | Substituierte triazolinone |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE792451A (fr) * | 1971-12-10 | 1973-06-08 | Ciba Geigy | Esters triazolyliques d'acides phosphores et produits pesticides qui encontiennent |
| BE792449A (fr) * | 1971-12-10 | 1973-06-08 | Ciba Geigy | Esters triazolyliques d'acides oxygenes du phosphore et produits pesticides qui en renferment |
| IL42316A (en) * | 1972-06-16 | 1976-02-29 | Ciba Geigy Ag | Triazolyl organophosphorus derivatives,their manufacture and their use as pesticides |
| DE2250572A1 (de) * | 1972-10-14 | 1974-04-18 | Bayer Ag | N,n-dimethyl-o-triazolyl-carbaminsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| NL7316469A (en:Method) * | 1972-12-08 | 1974-06-11 | ||
| DE2301400C2 (de) * | 1973-01-12 | 1984-12-13 | Bayer Ag, 5090 Leverkusen | 0-Triazolyl-thionophosphor(phosphon)-säureester und -esteramide, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide |
-
1974
- 1974-08-29 CH CH1177174A patent/CH601266A5/xx not_active IP Right Cessation
-
1975
- 1975-07-31 NZ NZ178271A patent/NZ178271A/xx unknown
- 1975-08-15 CS CS755621A patent/CS193522B2/cs unknown
- 1975-08-18 SU SU7502163216A patent/SU577989A3/ru active
- 1975-08-25 NL NL7510012A patent/NL7510012A/xx not_active Application Discontinuation
- 1975-08-26 DE DE19752537973 patent/DE2537973A1/de active Granted
- 1975-08-27 HU HU75CI00001600A patent/HU172771B/hu unknown
- 1975-08-27 CA CA234,232A patent/CA1070696A/en not_active Expired
- 1975-08-27 GB GB35411/75A patent/GB1512456A/en not_active Expired
- 1975-08-27 DD DD188052A patent/DD122535A5/xx unknown
- 1975-08-28 AU AU84345/75A patent/AU499371B2/en not_active Expired
- 1975-08-28 AT AT664775A patent/AT342587B/de active
- 1975-08-28 ZA ZA00755512A patent/ZA755512B/xx unknown
- 1975-08-28 BE BE159531A patent/BE832830A/xx not_active IP Right Cessation
- 1975-08-28 IL IL48008A patent/IL48008A/xx unknown
- 1975-08-28 FR FR7526487A patent/FR2283132A1/fr active Granted
- 1975-08-28 ES ES440532A patent/ES440532A1/es not_active Expired
- 1975-08-29 JP JP50104879A patent/JPS5910351B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2158734C2 (ru) * | 1994-11-21 | 2000-11-10 | Байер Аг | Производные триазолила, способ их получения и фунгицидное средство |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5910351B2 (ja) | 1984-03-08 |
| DE2537973A1 (de) | 1976-03-11 |
| NZ178271A (en) | 1978-04-03 |
| GB1512456A (en) | 1978-06-01 |
| JPS5148668A (en) | 1976-04-26 |
| CS193522B2 (en) | 1979-10-31 |
| IL48008A0 (en) | 1975-11-25 |
| AU499371B2 (en) | 1979-04-12 |
| BE832830A (fr) | 1976-03-01 |
| AT342587B (de) | 1978-04-10 |
| DD122535A5 (en:Method) | 1976-10-12 |
| ZA755512B (en) | 1976-07-28 |
| ES440532A1 (es) | 1977-03-01 |
| HU172771B (hu) | 1978-12-28 |
| DE2537973C2 (en:Method) | 1989-04-06 |
| ATA664775A (de) | 1977-08-15 |
| AU8434575A (en) | 1977-03-03 |
| CH601266A5 (en:Method) | 1978-06-30 |
| NL7510012A (nl) | 1976-03-02 |
| FR2283132B1 (en:Method) | 1978-04-07 |
| FR2283132A1 (fr) | 1976-03-26 |
| CA1070696A (en) | 1980-01-29 |
| IL48008A (en) | 1979-07-25 |
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