GB1226981A - - Google Patents
Info
- Publication number
- GB1226981A GB1226981A GB1226981DA GB1226981A GB 1226981 A GB1226981 A GB 1226981A GB 1226981D A GB1226981D A GB 1226981DA GB 1226981 A GB1226981 A GB 1226981A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- alkyl
- reacting
- acid
- oco
- 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
- 150000001875 compounds Chemical class 0.000 abstract 23
- 125000000217 alkyl group Chemical group 0.000 abstract 9
- 239000002253 acid Substances 0.000 abstract 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 4
- 239000000460 chlorine Substances 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 229910052794 bromium Inorganic materials 0.000 abstract 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 2
- 150000002240 furans Chemical class 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 150000007529 inorganic bases Chemical class 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 2
- 229930192474 thiophene Natural products 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052727 yttrium Inorganic materials 0.000 abstract 2
- HAYBUXDSSMBDAM-UHFFFAOYSA-N 2-(4-bromophenyl)-4-(chloromethyl)furan Chemical compound BrC1=CC=C(C=C1)C1=CC(=CO1)CCl HAYBUXDSSMBDAM-UHFFFAOYSA-N 0.000 abstract 1
- AIQBMPNKXCRWJE-UHFFFAOYSA-N 2-(chloromethyl)-5-(4-chlorophenyl)thiophene Chemical compound ClCC=1SC(=CC1)C1=CC=C(C=C1)Cl AIQBMPNKXCRWJE-UHFFFAOYSA-N 0.000 abstract 1
- QLNOZUXAMSOBQH-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)thiophen-2-yl]acetic acid Chemical compound S1C(CC(=O)O)=CC=C1C1=CC=C(Cl)C=C1 QLNOZUXAMSOBQH-UHFFFAOYSA-N 0.000 abstract 1
- LLFFWHNNSIXVAA-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)thiophen-2-yl]acetonitrile Chemical compound C(#N)CC=1SC(=CC1)C1=CC=C(C=C1)Cl LLFFWHNNSIXVAA-UHFFFAOYSA-N 0.000 abstract 1
- WKIDXYDOEHQUKE-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)thiophen-2-yl]propanenitrile Chemical compound S1C(C(C#N)C)=CC=C1C1=CC=C(Cl)C=C1 WKIDXYDOEHQUKE-UHFFFAOYSA-N 0.000 abstract 1
- IEMMBWWQXVXBEU-UHFFFAOYSA-N 2-acetylfuran Chemical compound CC(=O)C1=CC=CO1 IEMMBWWQXVXBEU-UHFFFAOYSA-N 0.000 abstract 1
- KRIILKQTJUOQCJ-UHFFFAOYSA-N 2-bromo-4-phenylpyridine Chemical compound C1=NC(Br)=CC(C=2C=CC=CC=2)=C1 KRIILKQTJUOQCJ-UHFFFAOYSA-N 0.000 abstract 1
- HMEYXBLESAXSBH-UHFFFAOYSA-N 2-methyl-5-phenylthiophene-3-carbonyl chloride Chemical compound ClC(=O)C1=C(C)SC(C=2C=CC=CC=2)=C1 HMEYXBLESAXSBH-UHFFFAOYSA-N 0.000 abstract 1
- SXGVYGKLJNCUDA-UHFFFAOYSA-N 2-methyl-5-phenylthiophene-3-carboxylic acid Chemical compound OC(=O)C1=C(C)SC(C=2C=CC=CC=2)=C1 SXGVYGKLJNCUDA-UHFFFAOYSA-N 0.000 abstract 1
- WIHYCXKAMGUUKP-UHFFFAOYSA-N 5-(4-chlorophenyl)-3-methylthiophen-2-ol Chemical compound OC=1SC(=CC=1C)C1=CC=C(C=C1)Cl WIHYCXKAMGUUKP-UHFFFAOYSA-N 0.000 abstract 1
- 238000006218 Arndt-Eistert homologation reaction Methods 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 238000005672 Willgerodt-Kindler rearrangement reaction Methods 0.000 abstract 1
- LTJWVDIIVGAWTN-UHFFFAOYSA-N [5-(4-bromophenyl)furan-3-yl]methanol Chemical compound BrC1=CC=C(C=C1)C1=CC(=CO1)CO LTJWVDIIVGAWTN-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 abstract 1
- -1 alkali metal acetates Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 abstract 1
- 239000012975 dibutyltin dilaurate Substances 0.000 abstract 1
- WPUBGBGSCQOOHW-UHFFFAOYSA-N ethyl 2-[5-(4-chlorophenyl)thiophen-2-yl]acetate Chemical compound ClC1=CC=C(C=C1)C1=CC=C(S1)CC(=O)OCC WPUBGBGSCQOOHW-UHFFFAOYSA-N 0.000 abstract 1
- VNYLRPNFFOFWAZ-UHFFFAOYSA-N ethyl 2-acetyl-4-(4-bromophenyl)-4-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)CC(=O)C1=CC=C(Br)C=C1 VNYLRPNFFOFWAZ-UHFFFAOYSA-N 0.000 abstract 1
- PJGMNNJKJBAOTD-UHFFFAOYSA-N ethyl 5-(4-bromophenyl)-2-methylfuran-3-carboxylate Chemical compound O1C(C)=C(C(=O)OCC)C=C1C1=CC=C(Br)C=C1 PJGMNNJKJBAOTD-UHFFFAOYSA-N 0.000 abstract 1
- 229960003750 ethyl chloride Drugs 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- SPLHJFSITONDMI-UHFFFAOYSA-N methyl 2-[5-(4-chlorophenyl)furan-2-yl]acetate Chemical compound O1C(CC(=O)OC)=CC=C1C1=CC=C(Cl)C=C1 SPLHJFSITONDMI-UHFFFAOYSA-N 0.000 abstract 1
- 229940050176 methyl chloride Drugs 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- ZAIUVLYDJAYZHE-UHFFFAOYSA-M sodium 2-[5-(4-chlorophenyl)thiophen-2-yl]acetate Chemical compound ClC1=CC=C(C=C1)C1=CC=C(S1)CC(=O)[O-].[Na+] ZAIUVLYDJAYZHE-UHFFFAOYSA-M 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 150000003577 thiophenes Chemical class 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
- C07D307/38—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 substituted hydrocarbon radicals attached to ring carbon atoms
-
- 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
- C07D307/38—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- 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
- C07D307/38—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1789568 | 1968-04-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1226981A true GB1226981A (enrdf_load_stackoverflow) | 1971-03-31 |
Family
ID=10103129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1226981D Expired GB1226981A (enrdf_load_stackoverflow) | 1968-04-16 | 1968-04-16 |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS516144B1 (enrdf_load_stackoverflow) |
| AT (1) | AT285594B (enrdf_load_stackoverflow) |
| CH (1) | CH553177A (enrdf_load_stackoverflow) |
| CS (1) | CS160101B2 (enrdf_load_stackoverflow) |
| GB (1) | GB1226981A (enrdf_load_stackoverflow) |
| PL (1) | PL80177B1 (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009030450A2 (en) | 2007-09-03 | 2009-03-12 | Syngenta Limited | Novel herbicides |
| EP2527333A1 (en) | 2007-06-28 | 2012-11-28 | Syngenta Limited | Pyrandione, thiopyrandione and cyclohexanetrione compounds having herbicidal properties |
| US20200255417A1 (en) * | 2017-08-31 | 2020-08-13 | Ahammune Biosciences Private Limited | Novel thiophene compounds, process for synthesis and use thereof |
-
1968
- 1968-04-16 GB GB1226981D patent/GB1226981A/en not_active Expired
-
1969
- 1969-04-02 PL PL13272469A patent/PL80177B1/pl unknown
- 1969-04-15 CS CS267669A patent/CS160101B2/cs unknown
- 1969-04-15 CH CH1351571A patent/CH553177A/xx not_active IP Right Cessation
- 1969-04-16 AT AT366869A patent/AT285594B/de not_active IP Right Cessation
-
1973
- 1973-06-26 JP JP7214473A patent/JPS516144B1/ja active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2527333A1 (en) | 2007-06-28 | 2012-11-28 | Syngenta Limited | Pyrandione, thiopyrandione and cyclohexanetrione compounds having herbicidal properties |
| WO2009030450A2 (en) | 2007-09-03 | 2009-03-12 | Syngenta Limited | Novel herbicides |
| US20200255417A1 (en) * | 2017-08-31 | 2020-08-13 | Ahammune Biosciences Private Limited | Novel thiophene compounds, process for synthesis and use thereof |
| US11739082B2 (en) * | 2017-08-31 | 2023-08-29 | Ahammune Biosciences Private Limited | Thiophene compounds, process for synthesis and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CS160101B2 (enrdf_load_stackoverflow) | 1975-02-28 |
| JPS516144B1 (enrdf_load_stackoverflow) | 1976-02-25 |
| AT285594B (de) | 1970-11-10 |
| CH553177A (de) | 1974-08-30 |
| PL80177B1 (enrdf_load_stackoverflow) | 1975-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |