DD220604A5 - Verfahren zur herstellung von 3-hydroxy-5-methylisoxazole - Google Patents

Verfahren zur herstellung von 3-hydroxy-5-methylisoxazole Download PDF

Info

Publication number: DD220604A5
Authority: DD; German Democratic Republic
Prior art keywords: reaction; diketene; hydroxylamine; acid; hydroxy
Prior art date: 1983-04-12

Application number

DD84261870A

Other languages

German (de)

English (en)

Inventor

Tadashi Murakami

Kazuo Tomita

Original Assignee

Sankyo Co

Priority date (The priority date 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 date listed.)

1983-04-12

Filing date

1984-04-11

Publication date

1985-04-03

1984-04-11 Application filed by Sankyo Co filed Critical Sankyo Co

1985-04-03 Publication of DD220604A5 publication Critical patent/DD220604A5/de

Links

KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims abstract description 6
238000000034 method Methods 0.000 title claims description 26
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims abstract description 35
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 33
239000011541 reaction mixture Substances 0.000 claims abstract description 13
238000010924 continuous production Methods 0.000 claims abstract description 6
238000006243 chemical reaction Methods 0.000 claims description 59
239000002253 acid Substances 0.000 claims description 19
239000000243 solution Substances 0.000 claims description 19
VCWRWMWHBSZKPM-UHFFFAOYSA-N n-hydroxy-3-oxobutanamide Chemical compound CC(=O)CC(=O)NO VCWRWMWHBSZKPM-UHFFFAOYSA-N 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 9
239000011259 mixed solution Substances 0.000 claims description 5
230000020477 pH reduction Effects 0.000 claims description 4
239000012670 alkaline solution Substances 0.000 claims description 2
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims 1
WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims 1
FBUNCJZQLGHASG-UHFFFAOYSA-N n-hydroxy-3-hydroxyiminobutanamide Chemical compound ON=C(C)CC(=O)NO FBUNCJZQLGHASG-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 11
239000000203 mixture Substances 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
230000018044 dehydration Effects 0.000 description 8
238000006297 dehydration reaction Methods 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
150000002443 hydroxylamines Chemical class 0.000 description 7
239000000047 product Substances 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000007363 ring formation reaction Methods 0.000 description 6
-1 O-substituted acetoacetohydroxamic acid Chemical class 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
238000007086 side reaction Methods 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
PYUQCOIVVOLGJK-UHFFFAOYSA-N 3-methyl-4h-1,2-oxazol-5-one Chemical compound CC1=NOC(=O)C1 PYUQCOIVVOLGJK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
238000010306 acid treatment Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000006798 ring closing metathesis reaction Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
AODKDNSWTJMJLU-UHFFFAOYSA-N 3-hydroxyiminobutanoic acid Chemical group ON=C(C)CC(O)=O AODKDNSWTJMJLU-UHFFFAOYSA-N 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
238000010923 batch production Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
230000008021 deposition Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000012434 nucleophilic reagent Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
238000005554 pickling Methods 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
239000002689 soil Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- C07D261/12—Oxygen 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD84261870A 1983-04-12 1984-04-11 Verfahren zur herstellung von 3-hydroxy-5-methylisoxazole DD220604A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP58063046A JPS59190977A (ja)	1983-04-12	1983-04-12	３−ヒドロキシ−５−メチルイソオキサゾ−ルの連続製法

Publications (1)

Publication Number	Publication Date
DD220604A5 true DD220604A5 (de)	1985-04-03

Family

ID=13217995

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84261870A DD220604A5 (de)	1983-04-12	1984-04-11	Verfahren zur herstellung von 3-hydroxy-5-methylisoxazole

Country Status (13)

Country	Link
US (1)	US4634774A (pl)
EP (1)	EP0125782B1 (pl)
JP (1)	JPS59190977A (pl)
AT (1)	ATE35984T1 (pl)
CA (1)	CA1218660A (pl)
DD (1)	DD220604A5 (pl)
DE (1)	DE3472956D1 (pl)
DK (1)	DK157400C (pl)
ES (1)	ES531527A0 (pl)
FI (1)	FI77239C (pl)
HU (1)	HU196383B (pl)
PL (1)	PL142923B1 (pl)
SU (1)	SU1405702A3 (pl)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1101132C (zh) *	1999-09-14	2003-02-12	贵州大学	恶霉灵原粉生产方法
CN117946022A (zh) *	2023-12-15	2024-04-30	青岛锐丰源化工有限公司	一种恶霉灵合成方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL130992C (pl) *	1964-09-14
DE1918253A1 (de) *	1969-04-03	1970-10-08	Sankyo Co	Verbessertes Verfahren zur Herstellung von 3-Hydroxyisoxazolverbindungen
GB1256835A (pl) *	1969-07-03	1971-12-15
DE1958252A1 (de) *	1969-11-20	1971-05-27	Huels Chemische Werke Ag	Verfahren zur Herstellung von 3-Methylisoxazol
DD142710A1 (de) *	1979-04-04	1980-07-09	Guenter Steimecke	Verfahren zur herstellung von isoxazol-4-carbonsaeuren

1983
- 1983-04-12 JP JP58063046A patent/JPS59190977A/ja active Granted
1984
- 1984-04-05 US US06/597,170 patent/US4634774A/en not_active Expired - Lifetime
- 1984-04-09 AT AT84302420T patent/ATE35984T1/de not_active IP Right Cessation
- 1984-04-09 EP EP84302420A patent/EP0125782B1/en not_active Expired
- 1984-04-09 DE DE8484302420T patent/DE3472956D1/de not_active Expired
- 1984-04-11 DD DD84261870A patent/DD220604A5/de unknown
- 1984-04-11 CA CA000451731A patent/CA1218660A/en not_active Expired
- 1984-04-11 SU SU3728852A patent/SU1405702A3/ru active
- 1984-04-11 ES ES531527A patent/ES531527A0/es active Granted
- 1984-04-12 PL PL1984247200A patent/PL142923B1/pl unknown
- 1984-04-12 DK DK190484A patent/DK157400C/da not_active IP Right Cessation
- 1984-04-12 FI FI841471A patent/FI77239C/fi not_active IP Right Cessation
- 1984-04-12 HU HU841442A patent/HU196383B/hu not_active IP Right Cessation

Also Published As

Publication number	Publication date
SU1405702A3 (ru)	1988-06-23
HU196383B (en)	1988-11-28
ES8603842A1 (es)	1985-09-01
EP0125782B1 (en)	1988-07-27
US4634774A (en)	1987-01-06
FI77239B (fi)	1988-10-31
CA1218660A (en)	1987-03-03
EP0125782A1 (en)	1984-11-21
DK157400B (da)	1990-01-02
JPS59190977A (ja)	1984-10-29
PL142923B1 (en)	1987-12-31
FI77239C (fi)	1989-02-10
FI841471L (fi)	1984-10-13
ATE35984T1 (de)	1988-08-15
HUT34738A (en)	1985-04-28
DK190484A (da)	1984-10-13
PL247200A1 (en)	1985-03-26
JPH045024B2 (pl)	1992-01-30
DK190484D0 (da)	1984-04-12
FI841471A0 (fi)	1984-04-12
DE3472956D1 (en)	1988-09-01
ES531527A0 (es)	1985-09-01
DK157400C (da)	1990-05-21

Publication	Publication Date	Title
DE2207699B2 (de)	1977-09-22	Verfahren zur herstellung von saeurealdehyden durch umlagerung der aus den entsprechenden ozoniden von cycloolefinen gebildeten peroxidderivate
EP0019227B1 (de)	1982-03-24	Verfahren zur Herstellung von Cyanhydrinacylaten von Aldehyden
DE2517054A1 (de)	1976-10-28	Verfahren zur herstellung von nicotinsaeureamid
DD220604A5 (de)	1985-04-03	Verfahren zur herstellung von 3-hydroxy-5-methylisoxazole
DE69009394T2 (de)	1994-12-22	Verfahren zur Herstellung von 3-Cyano-3,5,5-trimethyl-1-cyclohexanon.
DE1795651B2 (de)	1979-01-04	Verfahren zur Herstellung von 6-substituierten 23,5,6-Tetrahydroimidazo [2,1-bJ thiazolen
DE2950608C2 (pl)	1990-09-13
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