IL99048A - Method for preparing aromatic ester esters - Google Patents
Method for preparing aromatic ester estersInfo
- Publication number
- IL99048A IL99048A IL9904891A IL9904891A IL99048A IL 99048 A IL99048 A IL 99048A IL 9904891 A IL9904891 A IL 9904891A IL 9904891 A IL9904891 A IL 9904891A IL 99048 A IL99048 A IL 99048A
- Authority
- IL
- Israel
- Prior art keywords
- thiol
- alkyl
- chloride
- aromatic
- aromatic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- -1 aromatic thiol esters Chemical class 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000001504 aryl thiols Chemical class 0.000 claims abstract description 12
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 9
- 150000004820 halides Chemical class 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 150000001356 alkyl thiols Chemical class 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 150000007970 thio esters Chemical class 0.000 claims description 5
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- FKPSBYZGRQJIMO-UHFFFAOYSA-M benzyl(triethyl)azanium;hydroxide Chemical group [OH-].CC[N+](CC)(CC)CC1=CC=CC=C1 FKPSBYZGRQJIMO-UHFFFAOYSA-M 0.000 claims description 3
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 3
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims description 3
- SXAWRMKQZKPHNJ-UHFFFAOYSA-M tetrapentylazanium;chloride Chemical compound [Cl-].CCCCC[N+](CCCCC)(CCCCC)CCCCC SXAWRMKQZKPHNJ-UHFFFAOYSA-M 0.000 claims description 3
- FBEVECUEMUUFKM-UHFFFAOYSA-M tetrapropylazanium;chloride Chemical compound [Cl-].CCC[N+](CCC)(CCC)CCC FBEVECUEMUUFKM-UHFFFAOYSA-M 0.000 claims description 3
- QVOFCQBZXGLNAA-UHFFFAOYSA-M tributyl(methyl)azanium;hydroxide Chemical compound [OH-].CCCC[N+](C)(CCCC)CCCC QVOFCQBZXGLNAA-UHFFFAOYSA-M 0.000 claims description 3
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 claims description 2
- 229940093495 ethanethiol Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- SBKBDFUOZKKFRK-UHFFFAOYSA-N pyridine-3,5-dicarbonyl chloride Chemical compound ClC(=O)C1=CN=CC(C(Cl)=O)=C1 SBKBDFUOZKKFRK-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- YUBJPYNSGLJZPQ-UHFFFAOYSA-N Dithiopyr Chemical compound CSC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)SC)=C1CC(C)C YUBJPYNSGLJZPQ-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BOCQEKBKBUOBCR-UHFFFAOYSA-N 4-(2-methyliminohydrazinyl)benzoic acid Chemical compound CN=NNC1=CC=C(C(O)=O)C=C1 BOCQEKBKBUOBCR-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- MBVGZSSYNIBAKI-UHFFFAOYSA-N pyridine-2-carbothioic s-acid Chemical class OC(=S)C1=CC=CC=N1 MBVGZSSYNIBAKI-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- BKVFOAJKAAHXEZ-UHFFFAOYSA-N 3-o,5-o-dimethyl 2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)pyridine-3,5-dicarbothioate Chemical group COC(=S)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=S)OC)=C1CC(C)C BKVFOAJKAAHXEZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- PRNFLFIICMGARJ-UHFFFAOYSA-N carbonochloridic acid;pyridine Chemical compound OC(Cl)=O.C1=CC=NC=C1 PRNFLFIICMGARJ-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- KFGJUQRJVQDJHL-UHFFFAOYSA-N ethanethiol Chemical compound CCS.CCS KFGJUQRJVQDJHL-UHFFFAOYSA-N 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/83—Thioacids; Thioesters; Thioamides; Thioimides
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)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/623,821 US5071992A (en) | 1990-12-07 | 1990-12-07 | Process for preparation of aromatic thiol esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL99048A0 IL99048A0 (en) | 1992-07-15 |
| IL99048A true IL99048A (en) | 1995-12-31 |
Family
ID=24499529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9904891A IL99048A (en) | 1990-12-07 | 1991-08-01 | Method for preparing aromatic ester esters |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5071992A (de) |
| EP (1) | EP0561782B1 (de) |
| JP (1) | JP3058447B2 (de) |
| KR (1) | KR970002595B1 (de) |
| AT (1) | ATE136887T1 (de) |
| CA (1) | CA2093334A1 (de) |
| DE (1) | DE69118911T2 (de) |
| ES (1) | ES2086551T3 (de) |
| HU (1) | HUT63833A (de) |
| IE (1) | IE912727A1 (de) |
| IL (1) | IL99048A (de) |
| RU (1) | RU2014322C1 (de) |
| TW (1) | TW199888B (de) |
| WO (1) | WO1992010478A1 (de) |
| ZA (1) | ZA917190B (de) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH657124A5 (en) * | 1983-08-10 | 1986-08-15 | Lonza Ag | 3-Chloroisocinchomeronoyl chloride and a process for its preparation |
| US4692184A (en) * | 1984-04-24 | 1987-09-08 | Monsanto Company | 2,6-substituted pyridine compounds |
| US4698093A (en) * | 1984-11-06 | 1987-10-06 | Monsanto Company | Herbicidal (2 or 6)-fluoroalkyl-4-amino pyridine derivatives |
-
1990
- 1990-12-07 US US07/623,821 patent/US5071992A/en not_active Expired - Lifetime
-
1991
- 1991-08-01 HU HU931661A patent/HUT63833A/hu unknown
- 1991-08-01 DE DE69118911T patent/DE69118911T2/de not_active Expired - Fee Related
- 1991-08-01 CA CA002093334A patent/CA2093334A1/en not_active Abandoned
- 1991-08-01 WO PCT/US1991/005472 patent/WO1992010478A1/en not_active Ceased
- 1991-08-01 JP JP3514280A patent/JP3058447B2/ja not_active Expired - Fee Related
- 1991-08-01 IL IL9904891A patent/IL99048A/en not_active IP Right Cessation
- 1991-08-01 EP EP91914702A patent/EP0561782B1/de not_active Expired - Lifetime
- 1991-08-01 AT AT91914702T patent/ATE136887T1/de active
- 1991-08-01 ES ES91914702T patent/ES2086551T3/es not_active Expired - Lifetime
- 1991-08-01 IE IE272791A patent/IE912727A1/en unknown
- 1991-08-01 TW TW080106018A patent/TW199888B/zh active
- 1991-09-10 ZA ZA917190A patent/ZA917190B/xx unknown
- 1991-09-18 RU SU915001626A patent/RU2014322C1/ru active
-
1993
- 1993-06-05 KR KR93701693A patent/KR970002595B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2093334A1 (en) | 1992-06-08 |
| IL99048A0 (en) | 1992-07-15 |
| HUT63833A (en) | 1993-10-28 |
| HU9301661D0 (en) | 1993-09-28 |
| US5071992A (en) | 1991-12-10 |
| KR970002595B1 (en) | 1997-03-06 |
| WO1992010478A1 (en) | 1992-06-25 |
| IE912727A1 (en) | 1992-06-17 |
| RU2014322C1 (ru) | 1994-06-15 |
| DE69118911D1 (de) | 1996-05-23 |
| DE69118911T2 (de) | 1996-09-26 |
| ATE136887T1 (de) | 1996-05-15 |
| EP0561782A1 (de) | 1993-09-29 |
| JPH06503304A (ja) | 1994-04-14 |
| ES2086551T3 (es) | 1996-07-01 |
| JP3058447B2 (ja) | 2000-07-04 |
| EP0561782B1 (de) | 1996-04-17 |
| KR930703255A (ko) | 1993-11-29 |
| ZA917190B (en) | 1992-07-29 |
| TW199888B (de) | 1993-02-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| HP | Change in proprietorship | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |