ES376539A1 - PROCEDURE FOR THE PREPARATION OF FURAN-3-CARBOXAMIDE DERIVATIVES. - Google Patents
PROCEDURE FOR THE PREPARATION OF FURAN-3-CARBOXAMIDE DERIVATIVES.Info
- Publication number
- ES376539A1 ES376539A1 ES376539A ES376539A ES376539A1 ES 376539 A1 ES376539 A1 ES 376539A1 ES 376539 A ES376539 A ES 376539A ES 376539 A ES376539 A ES 376539A ES 376539 A1 ES376539 A1 ES 376539A1
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- alkyl
- general formula
- furan
- procedure
- 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
- GOLHZPOXCLTFRB-UHFFFAOYSA-N furan-3-carboxamide Chemical class NC(=O)C=1C=COC=1 GOLHZPOXCLTFRB-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005059 halophenyl group Chemical group 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 abstract 1
- 125000000335 thiazolyl group Chemical group 0.000 abstract 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)
Abstract
Procedure for the preparation of derivatives of furan-3-carboxamide, of general formula: **(See formula)** wherein X, Y, and Z are independently selected from H, NH2-, alkyl, substituted haloalkyl, alkenyl; X and Z are together α ω -alkylene, phenyl and substituted phenyl; R is chosen from H, alkyl, acyl, aroyl, and sulfenyl; R1 is chosen from phenyl, alkylphenyl, alkoxyphenyl, halophenyl, nitrophenyl, benzyl, bi-phenyl, alkyl, alkenyl, cycloalkyl, naphthyl, pyridyl, thiazolyl, furfurylmethyl and ethylene bis-; characterized in that it comprises reacting an α hydroxy ketone of the general formula: **(See formula)** where Y and Z are defined as above, with an acetamide of general formula: **(See formula)** wherein X, R and R1 are defined as above, in an inert solvent, in the presence of an active Friedel-Crafts reagent. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79910969A | 1969-02-13 | 1969-02-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES376539A1 true ES376539A1 (en) | 1972-04-16 |
Family
ID=25175061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES376539A Expired ES376539A1 (en) | 1969-02-13 | 1970-02-13 | PROCEDURE FOR THE PREPARATION OF FURAN-3-CARBOXAMIDE DERIVATIVES. |
Country Status (20)
| Country | Link |
|---|---|
| AT (1) | AT294060B (en) |
| BE (1) | BE745863A (en) |
| CA (1) | CA932334A (en) |
| CH (2) | CH567495A5 (en) |
| CS (1) | CS188869B2 (en) |
| DE (1) | DE2006472C2 (en) |
| DK (1) | DK134176B (en) |
| EG (1) | EG12357A (en) |
| ES (1) | ES376539A1 (en) |
| FR (1) | FR2068181A5 (en) |
| GB (1) | GB1303844A (en) |
| IL (1) | IL33880A (en) |
| LU (1) | LU60345A1 (en) |
| NL (1) | NL172061C (en) |
| NO (1) | NO134337C (en) |
| PL (1) | PL80863B1 (en) |
| RO (1) | RO57890A (en) |
| SE (1) | SE393985C (en) |
| TR (1) | TR16671A (en) |
| ZA (1) | ZA70828B (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3959481A (en) * | 1969-02-13 | 1976-05-25 | Uniroyal | Method of protecting plants from fungal diseases using furan-3-carboxamide derivatives |
| DE2019535C3 (en) * | 1970-04-23 | 1987-02-12 | Basf Ag, 6700 Ludwigshafen | 2,5-Dimethyl-furan-3-carboxylic acid cyclohexylamide and fungicidal agents containing this compound |
| BE795524A (en) * | 1972-02-16 | 1973-08-16 | Basf Ag | PROCESS FOR PREPARING ESTERS OF DIMETHYL-2,5-FURANNE-CARBOXYLIC-3 |
| GB1387652A (en) * | 1972-05-10 | 1975-03-19 | Shell Int Research | Process for preparing furan carboxamides |
| DE2703023A1 (en) * | 1977-01-26 | 1978-07-27 | Basf Ag | FURANDERIVATE |
| DE2800505A1 (en) | 1978-01-05 | 1979-07-19 | Consortium Elektrochem Ind | METHOD FOR PRODUCING SUBSTITUTED FURANES |
| DE2826013A1 (en) * | 1978-06-14 | 1980-01-03 | Basf Ag | METHOD FOR PRODUCING 2,5-DIMETHYLFURAN-3-CARBONIC ACID ALKYL ESTERS |
| DE10222884A1 (en) * | 2002-05-23 | 2003-12-04 | Bayer Cropscience Ag | furancarboxamides |
| US20050113566A1 (en) * | 2003-04-25 | 2005-05-26 | Player Mark R. | Inhibitors of C-FMS kinase |
| DE102004005786A1 (en) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | Haloalkylcarboxamide |
| DE102004005785A1 (en) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | 2-Halogenfuryl / thienyl-3-carboxamide |
| DE102004005787A1 (en) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | carboxamides |
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 (en) * | 1968-06-19 | 1971-05-27 | Basf Ag | Furan-3-carboxylic acid anilides and their use as a fungicide |
-
1969
- 1969-10-28 CA CA066031A patent/CA932334A/en not_active Expired
-
1970
- 1970-02-06 ZA ZA700828A patent/ZA70828B/en unknown
- 1970-02-09 GB GB608370A patent/GB1303844A/en not_active Expired
- 1970-02-10 IL IL33880A patent/IL33880A/en unknown
- 1970-02-11 SE SE7001749A patent/SE393985C/en unknown
- 1970-02-12 PL PL1970138768A patent/PL80863B1/pl unknown
- 1970-02-12 NO NO495/70A patent/NO134337C/no unknown
- 1970-02-12 CS CS70991A patent/CS188869B2/en unknown
- 1970-02-12 FR FR7005054A patent/FR2068181A5/fr not_active Expired
- 1970-02-12 BE BE745863D patent/BE745863A/en not_active IP Right Cessation
- 1970-02-12 DE DE2006472A patent/DE2006472C2/en not_active Expired
- 1970-02-12 NL NLAANVRAGE7002030,A patent/NL172061C/en not_active IP Right Cessation
- 1970-02-12 DK DK68870AA patent/DK134176B/en unknown
- 1970-02-13 CH CH1666673A patent/CH567495A5/xx not_active IP Right Cessation
- 1970-02-13 CH CH211370A patent/CH558349A/en not_active IP Right Cessation
- 1970-02-13 TR TR16671A patent/TR16671A/en unknown
- 1970-02-13 ES ES376539A patent/ES376539A1/en not_active Expired
- 1970-02-13 AT AT133670A patent/AT294060B/en not_active IP Right Cessation
- 1970-02-13 LU LU60345D patent/LU60345A1/xx unknown
- 1970-02-13 RO RO62460A patent/RO57890A/ro unknown
-
1976
- 1976-09-04 EG EG547/76A patent/EG12357A/en active
Also Published As
| Publication number | Publication date |
|---|---|
| LU60345A1 (en) | 1971-06-21 |
| CA932334A (en) | 1973-08-21 |
| IL33880A (en) | 1984-09-30 |
| GB1303844A (en) | 1973-01-24 |
| PL80863B1 (en) | 1975-08-30 |
| EG12357A (en) | 1978-09-30 |
| CH567495A5 (en) | 1975-10-15 |
| RO57890A (en) | 1975-08-15 |
| SE393985B (en) | 1977-05-31 |
| NL7002030A (en) | 1970-08-17 |
| TR16671A (en) | 1973-03-01 |
| DE2006472A1 (en) | 1970-08-27 |
| CH558349A (en) | 1975-01-31 |
| DK134176C (en) | 1977-02-28 |
| DE2006472C2 (en) | 1983-12-22 |
| NO134337B (en) | 1976-06-14 |
| IL33880A0 (en) | 1970-04-20 |
| NL172061B (en) | 1983-02-01 |
| AT294060B (en) | 1971-11-10 |
| NO134337C (en) | 1976-09-22 |
| FR2068181A5 (en) | 1971-08-20 |
| CS188869B2 (en) | 1979-03-30 |
| DK134176B (en) | 1976-09-27 |
| SE393985C (en) | 1980-12-22 |
| ZA70828B (en) | 1971-09-29 |
| NL172061C (en) | 1983-07-01 |
| BE745863A (en) | 1970-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19870212 |