JP2000502701A - 1―(2―フルオロ―フェニル)―1、2、4―トリアゾールの選択的塩素化 - Google Patents
1―(2―フルオロ―フェニル)―1、2、4―トリアゾールの選択的塩素化Info
- Publication number
- JP2000502701A JP2000502701A JP09524320A JP52432097A JP2000502701A JP 2000502701 A JP2000502701 A JP 2000502701A JP 09524320 A JP09524320 A JP 09524320A JP 52432097 A JP52432097 A JP 52432097A JP 2000502701 A JP2000502701 A JP 2000502701A
- Authority
- JP
- Japan
- Prior art keywords
- triazole
- fluorophenyl
- methyl
- oxo
- temperature
- 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.)
- Granted
Links
- 238000005660 chlorination reaction Methods 0.000 title abstract description 21
- GLLMNMAXIYOAKT-UHFFFAOYSA-N 1-(2-fluorophenyl)-1,2,4-triazole Chemical compound FC1=CC=CC=C1N1N=CN=C1 GLLMNMAXIYOAKT-UHFFFAOYSA-N 0.000 title description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 31
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 26
- 239000006227 byproduct Substances 0.000 claims abstract description 21
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 48
- 239000011541 reaction mixture Substances 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- -1 4-chloro-2-fluorophenyl Chemical group 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 238000010926 purge Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000002002 slurry Substances 0.000 claims description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- XLSXXXARCKJHOR-UHFFFAOYSA-N 5-methyl-1,2-dihydro-1,2,4-triazol-3-one Chemical compound CC1=NC(=O)NN1 XLSXXXARCKJHOR-UHFFFAOYSA-N 0.000 claims 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims 1
- 229910052753 mercury Inorganic materials 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract description 20
- 239000004009 herbicide Substances 0.000 abstract description 7
- 230000002363 herbicidal effect Effects 0.000 abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 3
- ZMKXWDPUXLPHCA-UHFFFAOYSA-N 3-(4-fluorophenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(F)C=C1 ZMKXWDPUXLPHCA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 18
- 238000004817 gas chromatography Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000003852 triazoles Chemical group 0.000 description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- IZMAYSIPWMNWIZ-UHFFFAOYSA-N 2-(2-fluorophenyl)-5-methyl-1h-1,2,4-triazol-3-one Chemical compound O=C1NC(C)=NN1C1=CC=CC=C1F IZMAYSIPWMNWIZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- BTGAATKPDODCIK-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-5-methyl-1h-1,2,4-triazol-3-one Chemical compound O=C1NC(C)=NN1C1=CC=C(Cl)C=C1F BTGAATKPDODCIK-UHFFFAOYSA-N 0.000 description 1
- LFPCKNVVYSDVSQ-UHFFFAOYSA-N 2-(5-amino-4-chloro-2-fluorophenyl)-4-(difluoromethyl)-5-methyl-1,2,4-triazol-3-one Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(N)=C(Cl)C=C1F LFPCKNVVYSDVSQ-UHFFFAOYSA-N 0.000 description 1
- FKVIYERFOLSTTM-UHFFFAOYSA-N 2-fluoro-n-phenylacetamide Chemical compound FCC(=O)NC1=CC=CC=C1 FKVIYERFOLSTTM-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000012905 Brassica oleracea var viridis Nutrition 0.000 description 1
- 244000064816 Brassica oleracea var. acephala Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229950004696 flusalan Drugs 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.フェニル環の4−位における1−(2−フルオロフェニル)−4、5−ジヒ ドロ−3−メチル-5−オキソ−1H−1、2、4−トリアゾール(「2−フル オロフェニル化合物」)の塩素化方法において、 a)周囲温度−50℃の範囲の温度で、温度が50℃を超えないような速度で、 アセトニトリル、N、N−ジメチルホルムアミド、ニトロメタン及びニトロベン ゼンから選ばれる溶媒中の1−(2−フルオロフェニル)−4、5−ジヒドロー 3−メチル−5−オキソ−1H−1、2、4−トリアゾールの撹拌スラリーに0 .8−1.6モル当量の塩素を加え、そして撹拌を1−10時間30−50℃で 続け; b)温度を30−50℃に維持しつつ1−6時間、溶媒が還流しそして塩化水素 副生物の殆どが排除されるように反応容器の圧力を低下させ; c)任意に、反応容器を窒素によりパージして反応混合物中の塩化水素濃度を1 %以下に低下させ; d)a、b及びcの工程を2回繰り返し; e)1−(4−クロロ−2−フルオロフェニル)−4、5−ジヒドロ−3−メチ ル−5−オキソ−1H−1、2、4−トリアゾールを回収することからなる方法 。 2.a)30−40℃の範囲の温度で、温度が35−40℃である速度で、アセ トニトリルの体積当たり2−フルオロフェニル化合物の重量%が5−70%の範 囲にある、アセトニトリル中の2−フルオロフェニル化合物の撹拌スラリーに0 .9−1.5モル当量の塩素を添加し、そして3−6時間30−40℃で撹拌を 続け; b)温度を35−40℃に維持しつつ2−4時間、溶媒が還流しそして塩化水素 副生物の殆どが排除されるように反応容器の圧力を低下させる ことからなる請求項1の方法。 3.a−dの段階が減圧で実施される請求項2の方法。 4.減圧が水銀柱300−500mmの範囲にある請求項3の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US932095P | 1995-12-29 | 1995-12-29 | |
US60/009,320 | 1995-12-29 | ||
PCT/US1996/018600 WO1997024337A1 (en) | 1995-12-29 | 1996-11-20 | Selective chlorination of a 1-(2-fluorophenyl)-1,2,4-triazole |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2000502701A true JP2000502701A (ja) | 2000-03-07 |
JP3802566B2 JP3802566B2 (ja) | 2006-07-26 |
Family
ID=21736931
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP52432097A Expired - Fee Related JP3802566B2 (ja) | 1995-12-29 | 1996-11-20 | 1―(2―フルオロ―フェニル)―1、2、4―トリアゾールの選択的塩素化 |
Country Status (18)
Country | Link |
---|---|
US (1) | US5965742A (ja) |
EP (1) | EP0889882B1 (ja) |
JP (1) | JP3802566B2 (ja) |
KR (1) | KR100454802B1 (ja) |
CN (1) | CN1067383C (ja) |
AT (1) | ATE271549T1 (ja) |
AU (1) | AU710982B2 (ja) |
BR (1) | BR9612366A (ja) |
CA (1) | CA2241632C (ja) |
CZ (1) | CZ292185B6 (ja) |
DE (1) | DE69632966T2 (ja) |
ES (1) | ES2224185T3 (ja) |
HK (1) | HK1017678A1 (ja) |
HU (1) | HU225546B1 (ja) |
MX (1) | MX9805188A (ja) |
PL (1) | PL186048B1 (ja) |
RU (1) | RU2167870C2 (ja) |
WO (1) | WO1997024337A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103965124A (zh) * | 2014-04-29 | 2014-08-06 | 安徽苏启化工有限公司 | 一种***啉酮合成方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN85106905A (zh) * | 1985-08-08 | 1987-02-04 | Fmc公司 | 含有1-芳基-δ2-1,2,4,-***啉-5-酮类的除草剂及其制备方法 |
WO1988009617A1 (en) * | 1987-06-12 | 1988-12-15 | Fmc Corporation | 1-(4-chloro-2-fluoro-5-methoxyphenyl)-3-methyl-4-difluoromethyl-delta2-1,2,4-triazolin-5-one as herbicidal agent |
US5256793A (en) * | 1992-05-13 | 1993-10-26 | Fmc Corporation | Triazolinone ring formation in tert-butanol |
US5468868A (en) * | 1993-12-16 | 1995-11-21 | Fmc Corporation | Process for the selective chlorination of 4,5-dihydro-1-phenyl-1H-1,2,4-triazol-5-one |
US5438149A (en) * | 1994-05-27 | 1995-08-01 | Fmc Corporation | Difluoromethylation of a phenyl triazolinone |
US5449784A (en) * | 1994-06-22 | 1995-09-12 | Fmc Corporation | Method of preparing aryl triazolinones with trialkyl orthoacetates |
-
1996
- 1996-11-20 ES ES96941410T patent/ES2224185T3/es not_active Expired - Lifetime
- 1996-11-20 CZ CZ19981646A patent/CZ292185B6/cs not_active IP Right Cessation
- 1996-11-20 CA CA002241632A patent/CA2241632C/en not_active Expired - Fee Related
- 1996-11-20 EP EP96941410A patent/EP0889882B1/en not_active Expired - Lifetime
- 1996-11-20 US US09/091,867 patent/US5965742A/en not_active Expired - Fee Related
- 1996-11-20 RU RU98114503/04A patent/RU2167870C2/ru not_active IP Right Cessation
- 1996-11-20 BR BR9612366A patent/BR9612366A/pt not_active IP Right Cessation
- 1996-11-20 JP JP52432097A patent/JP3802566B2/ja not_active Expired - Fee Related
- 1996-11-20 WO PCT/US1996/018600 patent/WO1997024337A1/en active IP Right Grant
- 1996-11-20 AT AT96941410T patent/ATE271549T1/de not_active IP Right Cessation
- 1996-11-20 DE DE69632966T patent/DE69632966T2/de not_active Expired - Fee Related
- 1996-11-20 KR KR10-1998-0704897A patent/KR100454802B1/ko not_active IP Right Cessation
- 1996-11-20 AU AU10562/97A patent/AU710982B2/en not_active Ceased
- 1996-11-20 CN CN96198753A patent/CN1067383C/zh not_active Expired - Fee Related
- 1996-11-20 HU HU9902053A patent/HU225546B1/hu not_active IP Right Cessation
- 1996-11-20 PL PL96327601A patent/PL186048B1/pl not_active IP Right Cessation
-
1998
- 1998-06-25 MX MX9805188A patent/MX9805188A/es unknown
-
1999
- 1999-06-24 HK HK99102718A patent/HK1017678A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
EP0889882B1 (en) | 2004-07-21 |
ATE271549T1 (de) | 2004-08-15 |
US5965742A (en) | 1999-10-12 |
EP0889882A1 (en) | 1999-01-13 |
KR19990076773A (ko) | 1999-10-15 |
CZ164698A3 (cs) | 1998-09-16 |
JP3802566B2 (ja) | 2006-07-26 |
CN1067383C (zh) | 2001-06-20 |
DE69632966D1 (de) | 2004-08-26 |
WO1997024337A1 (en) | 1997-07-10 |
CN1203591A (zh) | 1998-12-30 |
DE69632966T2 (de) | 2005-08-25 |
HUP9902053A3 (en) | 2000-01-28 |
PL186048B1 (pl) | 2003-09-30 |
AU1056297A (en) | 1997-07-28 |
MX9805188A (es) | 1998-10-31 |
EP0889882A4 (en) | 2000-01-26 |
AU710982B2 (en) | 1999-10-07 |
BR9612366A (pt) | 1999-07-13 |
CA2241632C (en) | 2005-10-18 |
CZ292185B6 (cs) | 2003-08-13 |
CA2241632A1 (en) | 1997-07-10 |
ES2224185T3 (es) | 2005-03-01 |
KR100454802B1 (ko) | 2004-12-31 |
HU225546B1 (en) | 2007-03-28 |
HK1017678A1 (en) | 1999-11-26 |
HUP9902053A2 (hu) | 1999-11-29 |
RU2167870C2 (ru) | 2001-05-27 |
PL327601A1 (en) | 1998-12-21 |
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