DD145270A5 - Verfahren zur herstellung von o-methyl-n-cyclohexyl-2,5-dimethylfuran-3-hydroxamsaeure ueber n-cyclohexyl-n-methoxyacetoacetamid - Google Patents

Verfahren zur herstellung von o-methyl-n-cyclohexyl-2,5-dimethylfuran-3-hydroxamsaeure ueber n-cyclohexyl-n-methoxyacetoacetamid Download PDF

Info

Publication number: DD145270A5
Authority: DD; German Democratic Republic
Prior art keywords: cyclohexyl; methyl; dimethylfuran; methoxyacetoacetamide; hydroxamic acid
Prior art date: 1978-07-21

Application number

DD79214402A

Other languages

German (de)

English (en)

Inventor

Friedrich Linhart

Bjoern Girgensohn

Bernd Zeeh

Original Assignee

Basf Ag

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.)

1978-07-21

Filing date

1979-07-17

Publication date

1980-12-03

1979-07-17 Application filed by Basf Ag filed Critical Basf Ag

1980-12-03 Publication of DD145270A5 publication Critical patent/DD145270A5/de

Links

NPNAMLFXWGDFTD-UHFFFAOYSA-N n-cyclohexyl-n-methoxy-3-oxobutanamide Chemical compound CC(=O)CC(=O)N(OC)C1CCCCC1 NPNAMLFXWGDFTD-UHFFFAOYSA-N 0.000 title claims abstract description 13
QTDRLOKFLJJHTG-UHFFFAOYSA-N Furmecyclox Chemical compound C1=C(C)OC(C)=C1C(=O)N(OC)C1CCCCC1 QTDRLOKFLJJHTG-UHFFFAOYSA-N 0.000 title claims abstract description 10
238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 claims abstract description 8
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
GOKZDNKPQVQQHT-UHFFFAOYSA-N n-methoxycyclohexanamine Chemical compound CONC1CCCCC1 GOKZDNKPQVQQHT-UHFFFAOYSA-N 0.000 claims description 4
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 3
229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 3
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
239000003377 acid catalyst Substances 0.000 claims description 2
238000010533 azeotropic distillation Methods 0.000 claims description 2
239000011230 binding agent Substances 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
239000002904 solvent Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
-1 benzines Chemical compound 0.000 description 4
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
239000003085 diluting agent Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
RWORXZHVOUPMMM-UHFFFAOYSA-N 2,5-dimethylfuran-3-carbonyl chloride Chemical compound CC1=CC(C(Cl)=O)=C(C)O1 RWORXZHVOUPMMM-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
239000012043 crude product Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000007037 hydroformylation reaction Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
DYEHJUARZNVANY-UHFFFAOYSA-N n-cyclohexyl-n-hydroxy-2,4,5-trimethylfuran-3-carboxamide Chemical compound CC1=C(C)OC(C)=C1C(=O)N(O)C1CCCCC1 DYEHJUARZNVANY-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
150000003738 xylenes Chemical class 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
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Furan Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

DD79214402A 1978-07-21 1979-07-17 Verfahren zur herstellung von o-methyl-n-cyclohexyl-2,5-dimethylfuran-3-hydroxamsaeure ueber n-cyclohexyl-n-methoxyacetoacetamid DD145270A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782832102 DE2832102A1 (de)	1978-07-21	1978-07-21	N-cyclohexyl-n-methoxyacetoacetamid, verfahren zu seiner herstellung und seine verwendung zur herstellung von furan- derivaten

Publications (1)

Publication Number	Publication Date
DD145270A5 true DD145270A5 (de)	1980-12-03

Family

ID=6045023

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79214402A DD145270A5 (de)	1978-07-21	1979-07-17	Verfahren zur herstellung von o-methyl-n-cyclohexyl-2,5-dimethylfuran-3-hydroxamsaeure ueber n-cyclohexyl-n-methoxyacetoacetamid

Country Status (10)

Country	Link
US (1)	US4240973A (da)
EP (1)	EP0008370B1 (da)
JP (1)	JPS5517393A (da)
AT (1)	ATE453T1 (da)
CA (1)	CA1150311A (da)
DD (1)	DD145270A5 (da)
DE (2)	DE2832102A1 (da)
DK (1)	DK306479A (da)
HU (1)	HU180682B (da)
IL (1)	IL57838A (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH04113924A (ja) *	1990-09-03	1992-04-15	Nichibei Kaihatsu:Kk	自動車用ブラインド及びこれの製造方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1931386A1 (de) *	1969-06-20	1970-12-23	Basf Ag	N-acylierte Cycloalkylhydroxylamine
JPS5749552B2 (da) *	1972-06-07	1982-10-22
GB1517960A (en) *	1974-11-21	1978-07-19	Basf Ag	Furanhydroxamic acid derivatives useful as fungicides

1978
- 1978-07-21 DE DE19782832102 patent/DE2832102A1/de active Pending
1979
- 1979-07-17 DD DD79214402A patent/DD145270A5/de unknown
- 1979-07-18 DE DE7979102534T patent/DE2961506D1/de not_active Expired
- 1979-07-18 AT AT79102534T patent/ATE453T1/de not_active IP Right Cessation
- 1979-07-18 CA CA000332051A patent/CA1150311A/en not_active Expired
- 1979-07-18 EP EP79102534A patent/EP0008370B1/de not_active Expired
- 1979-07-19 IL IL57838A patent/IL57838A/xx not_active IP Right Cessation
- 1979-07-20 DK DK306479A patent/DK306479A/da not_active Application Discontinuation
- 1979-07-20 HU HU79BA3822A patent/HU180682B/hu not_active IP Right Cessation
- 1979-07-20 JP JP9175779A patent/JPS5517393A/ja active Granted
- 1979-07-23 US US06/059,775 patent/US4240973A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP0008370B1 (de)	1981-12-02
DK306479A (da)	1980-01-22
IL57838A0 (en)	1979-11-30
DE2832102A1 (de)	1980-01-31
JPS5517393A (en)	1980-02-06
DE2961506D1 (en)	1982-01-28
EP0008370A2 (de)	1980-03-05
ATE453T1 (de)	1981-12-15
HU180682B (en)	1983-04-29
CA1150311A (en)	1983-07-19
US4240973A (en)	1980-12-23
EP0008370A3 (en)	1980-05-28
IL57838A (en)	1982-12-31
JPS6219421B2 (da)	1987-04-28

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