DE2006472C2 - Verfahren zur Herstellung von 2-Methylfuran-3-carboxamiden - Google Patents
Verfahren zur Herstellung von 2-Methylfuran-3-carboxamidenInfo
- Publication number
- DE2006472C2 DE2006472C2 DE2006472A DE2006472A DE2006472C2 DE 2006472 C2 DE2006472 C2 DE 2006472C2 DE 2006472 A DE2006472 A DE 2006472A DE 2006472 A DE2006472 A DE 2006472A DE 2006472 C2 DE2006472 C2 DE 2006472C2
- Authority
- DE
- Germany
- Prior art keywords
- methylfuran
- mol
- carboxamides
- general formula
- water
- 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
Links
- ZTXBBUFJNINBPD-UHFFFAOYSA-N 2-methylfuran-3-carboxamide Chemical class CC=1OC=CC=1C(N)=O ZTXBBUFJNINBPD-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 9
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 claims description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910008433 SnCU Inorganic materials 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- -1 methoxyphenyl Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 11
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 5
- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 2
- 241000221577 Uromyces appendiculatus Species 0.000 description 2
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- ZWJNEYVWPYIKMB-UHFFFAOYSA-N methfuroxam Chemical compound CC1=C(C)OC(C)=C1C(=O)NC1=CC=CC=C1 ZWJNEYVWPYIKMB-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- NMRDELHCVAOOPZ-UHFFFAOYSA-N 2,4-dimethyl-n-phenylfuran-3-carboxamide Chemical compound CC1=COC(C)=C1C(=O)NC1=CC=CC=C1 NMRDELHCVAOOPZ-UHFFFAOYSA-N 0.000 description 1
- 241000213004 Alternaria solani Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 241000221566 Ustilago Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 244000144980 herd Species 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- KYYRTDXOHQYZPO-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=CC=C1NC(=O)CC(C)=O KYYRTDXOHQYZPO-UHFFFAOYSA-N 0.000 description 1
- TVZIWRMELPWPPR-UHFFFAOYSA-N n-(2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C TVZIWRMELPWPPR-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 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)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79910969A | 1969-02-13 | 1969-02-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2006472A1 DE2006472A1 (de) | 1970-08-27 |
| DE2006472C2 true DE2006472C2 (de) | 1983-12-22 |
Family
ID=25175061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2006472A Expired DE2006472C2 (de) | 1969-02-13 | 1970-02-12 | Verfahren zur Herstellung von 2-Methylfuran-3-carboxamiden |
Country Status (20)
| Country | Link |
|---|---|
| AT (1) | AT294060B (en, 2012) |
| BE (1) | BE745863A (en, 2012) |
| CA (1) | CA932334A (en, 2012) |
| CH (2) | CH558349A (en, 2012) |
| CS (1) | CS188869B2 (en, 2012) |
| DE (1) | DE2006472C2 (en, 2012) |
| DK (1) | DK134176B (en, 2012) |
| EG (1) | EG12357A (en, 2012) |
| ES (1) | ES376539A1 (en, 2012) |
| FR (1) | FR2068181A5 (en, 2012) |
| GB (1) | GB1303844A (en, 2012) |
| IL (1) | IL33880A (en, 2012) |
| LU (1) | LU60345A1 (en, 2012) |
| NL (1) | NL172061C (en, 2012) |
| NO (1) | NO134337C (en, 2012) |
| PL (1) | PL80863B1 (en, 2012) |
| RO (1) | RO57890A (en, 2012) |
| SE (1) | SE393985C (en, 2012) |
| TR (1) | TR16671A (en, 2012) |
| ZA (1) | ZA70828B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2006471A1 (de) * | 1969-02-13 | 1970-08-27 | Uniroyal, Inc., New York, N.Y.(V. St.A.); Uniroyal, Ltd., Montreal, Quebec (Kanada) | Schädlingsbekämpfungsmittel |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2019535C3 (de) * | 1970-04-23 | 1987-02-12 | Basf Ag, 6700 Ludwigshafen | 2,5-Dimethyl-furan-3-carbonsäure-cyclohexylamid und diese Verbindung enthaltende fungizide Mittel |
| BE795524A (fr) * | 1972-02-16 | 1973-08-16 | Basf Ag | Procede de preparation d'esters de l'acide dimethyl-2,5-furanne-carboxylique-3 |
| GB1387652A (en) * | 1972-05-10 | 1975-03-19 | Shell Int Research | Process for preparing furan carboxamides |
| DE2703023A1 (de) * | 1977-01-26 | 1978-07-27 | Basf Ag | Furanderivate |
| DE2800505A1 (de) | 1978-01-05 | 1979-07-19 | Consortium Elektrochem Ind | Verfahren zur herstellung von substituierten furanen |
| DE2826013A1 (de) * | 1978-06-14 | 1980-01-03 | Basf Ag | Verfahren zur herstellung von 2,5-dimethylfuran-3-carbonsaeurealkylestern |
| DE10222884A1 (de) | 2002-05-23 | 2003-12-04 | Bayer Cropscience Ag | Furancarboxamide |
| US20050113566A1 (en) * | 2003-04-25 | 2005-05-26 | Player Mark R. | Inhibitors of C-FMS kinase |
| DE102004005785A1 (de) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | 2-Halogenfuryl/thienyl-3-carboxamide |
| DE102004005787A1 (de) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | Carboxamide |
| DE102004005786A1 (de) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | Haloalkylcarboxamide |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1215066A (en) * | 1968-03-25 | 1970-12-09 | Shell Int Research | Acrylamides and their use as fungicides |
| DE1768686B1 (de) * | 1968-06-19 | 1971-05-27 | Basf Ag | Furan-3-carbonsaeureanilide und deren Verwendung als Fungizid |
-
1969
- 1969-10-28 CA CA066031A patent/CA932334A/en not_active Expired
-
1970
- 1970-02-06 ZA ZA700828A patent/ZA70828B/xx unknown
- 1970-02-09 GB GB608370A patent/GB1303844A/en not_active Expired
- 1970-02-10 IL IL33880A patent/IL33880A/xx unknown
- 1970-02-11 SE SE7001749A patent/SE393985C/xx unknown
- 1970-02-12 DK DK68870AA patent/DK134176B/da unknown
- 1970-02-12 DE DE2006472A patent/DE2006472C2/de not_active Expired
- 1970-02-12 NO NO495/70A patent/NO134337C/no unknown
- 1970-02-12 PL PL1970138768A patent/PL80863B1/pl unknown
- 1970-02-12 CS CS70991A patent/CS188869B2/cs unknown
- 1970-02-12 BE BE745863D patent/BE745863A/xx not_active IP Right Cessation
- 1970-02-12 FR FR7005054A patent/FR2068181A5/fr not_active Expired
- 1970-02-12 NL NLAANVRAGE7002030,A patent/NL172061C/xx not_active IP Right Cessation
- 1970-02-13 LU LU60345D patent/LU60345A1/xx unknown
- 1970-02-13 CH CH211370A patent/CH558349A/xx not_active IP Right Cessation
- 1970-02-13 AT AT133670A patent/AT294060B/de not_active IP Right Cessation
- 1970-02-13 ES ES376539A patent/ES376539A1/es not_active Expired
- 1970-02-13 RO RO62460A patent/RO57890A/ro unknown
- 1970-02-13 TR TR16671A patent/TR16671A/xx unknown
- 1970-02-13 CH CH1666673A patent/CH567495A5/xx not_active IP Right Cessation
-
1976
- 1976-09-04 EG EG547/76A patent/EG12357A/xx active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2006471A1 (de) * | 1969-02-13 | 1970-08-27 | Uniroyal, Inc., New York, N.Y.(V. St.A.); Uniroyal, Ltd., Montreal, Quebec (Kanada) | Schädlingsbekämpfungsmittel |
Also Published As
| Publication number | Publication date |
|---|---|
| SE393985B (sv) | 1977-05-31 |
| TR16671A (tr) | 1973-03-01 |
| NL172061C (nl) | 1983-07-01 |
| GB1303844A (en, 2012) | 1973-01-24 |
| NL172061B (nl) | 1983-02-01 |
| CH567495A5 (en, 2012) | 1975-10-15 |
| IL33880A0 (en) | 1970-04-20 |
| LU60345A1 (en, 2012) | 1971-06-21 |
| DK134176B (da) | 1976-09-27 |
| NL7002030A (en, 2012) | 1970-08-17 |
| CA932334A (en) | 1973-08-21 |
| BE745863A (fr) | 1970-08-12 |
| CH558349A (de) | 1975-01-31 |
| FR2068181A5 (en, 2012) | 1971-08-20 |
| ZA70828B (en) | 1971-09-29 |
| CS188869B2 (en) | 1979-03-30 |
| ES376539A1 (es) | 1972-04-16 |
| EG12357A (en) | 1978-09-30 |
| RO57890A (en, 2012) | 1975-08-15 |
| NO134337C (en, 2012) | 1976-09-22 |
| AT294060B (de) | 1971-11-10 |
| DK134176C (en, 2012) | 1977-02-28 |
| NO134337B (en, 2012) | 1976-06-14 |
| IL33880A (en) | 1984-09-30 |
| PL80863B1 (en, 2012) | 1975-08-30 |
| SE393985C (sv) | 1980-12-22 |
| DE2006472A1 (de) | 1970-08-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE887506C (de) | Verfahren zur Herstellung von organischen Verbindungen | |
| DE2006472C2 (de) | Verfahren zur Herstellung von 2-Methylfuran-3-carboxamiden | |
| DE2025961C3 (de) | Verfahren zur Herstellung von N-(M-Dialkyl-3-chloracetonyl)-benzamiden und Derivate von N-(],l-Dimethyl-3-chloracetonyl)-benzamid | |
| DE2437882C3 (de) | Verfahren zur Herstellung von Estern des 3-Phenoxybenzylalkohols | |
| DE1951032C3 (de) | Verfahren zur Herstellung von Cyanessigsäureestern | |
| DE1468872A1 (de) | Verfahren zur Herstellung von 2,4-Dicyanobuten-(1) | |
| DE1670514B2 (de) | Katalytisches Verfahren zur Herstellung von Pyridin | |
| DE60025614T2 (de) | Verfahren zur herstellung von n-alkyl-bis(thiazolyl)sulfenimiden | |
| EP0017832B1 (de) | Verfahren zur Herstellung von 5-Brom-5-nitro-1,3-dioxan | |
| DE2804263B2 (de) | Verfahren zur Herstellung von Indolin-Derivaten | |
| DE2633204A1 (de) | Verfahren zur herstellung von benzylnatrium, phenylessigsaeure und derivaten derselben | |
| AT259562B (de) | Verfahren zur Herstellung von Benzodiazepin-Derivaten | |
| DE2233862B2 (de) | Verfahren zur herstellung von dimethylmaleinsaeureanhydrid | |
| DE1958238C (de) | l-Oxy-S^-dibrom-ö-halogen-thiochromanone | |
| AT230902B (de) | Verfahren zur Herstellung des neuen 0,0-Dimethyl-0(4-cyanphenyl)-thionophosphorsäureesters | |
| DE912217C (de) | Verfahren zur Herstellung von bisquaternaeren Salzen N-substituierter Amide von Pyridinmonocarbonsaeuren mit Alkylendihalogeniden | |
| DE1720519C3 (de) | Verfahren zur Herstellung von Polyestern | |
| AT230378B (de) | Verfahren zur Herstellung von neuen diquartären α,ω-Bis-[pyridyl-(4)-thio]-alkanen und -dialkyläthern | |
| AT231471B (de) | Verfahren zur Herstellung von neuen Thionothiolphosphorsäureestern | |
| DE317755C (en, 2012) | ||
| DE1468167B2 (de) | Basische ester bicyclischer dicarbonsaeuren, ihre saeureadditionssalze und bisquaternaeren ammoniumverbindungen, sowie verfahren zur herstellung derselben | |
| DE1137028B (de) | Verfahren zur Herstellung trisubstituierter s-Triazine | |
| AT262962B (de) | Verfahren zur Herstellung neuer Cyclopropancarbonsäureester | |
| DE2414794C3 (de) | Verfahren zur Herstellung von optisch aktivem Allethrolon | |
| AT227696B (de) | Verfahren zur Herstellung von 2-Amino-oxazolen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: BERENDT, T., DIPL.-CHEM. DR. LEYH, H., DIPL.-ING. |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |