GB1594450A - 1,3-oxathiolane sulphoxides and their use in the preparation of 5,6-dihydro-2-methyl-1,4-oxathiin derivatives - Google Patents
1,3-oxathiolane sulphoxides and their use in the preparation of 5,6-dihydro-2-methyl-1,4-oxathiin derivatives Download PDFInfo
- Publication number
- GB1594450A GB1594450A GB17940/78A GB1794078A GB1594450A GB 1594450 A GB1594450 A GB 1594450A GB 17940/78 A GB17940/78 A GB 17940/78A GB 1794078 A GB1794078 A GB 1794078A GB 1594450 A GB1594450 A GB 1594450A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- oxathiolane
- benzene
- sulfoxide
- 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
- 238000002360 preparation method Methods 0.000 title claims description 11
- WJJSZTJGFCFNKI-UHFFFAOYSA-N 1,3-oxathiolane Chemical compound C1CSCO1 WJJSZTJGFCFNKI-UHFFFAOYSA-N 0.000 title claims description 9
- YZVJOJNVIJLQAY-UHFFFAOYSA-N 6-methyl-2,3-dihydro-1,4-oxathiine Chemical class CC1=CSCCO1 YZVJOJNVIJLQAY-UHFFFAOYSA-N 0.000 title claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 34
- 150000003462 sulfoxides Chemical class 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 27
- -1 carboxyphenyl Chemical group 0.000 claims description 20
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 239000007832 Na2SO4 Substances 0.000 claims description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 9
- 235000011152 sodium sulphate Nutrition 0.000 claims description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- NHVHYFAWHCJELN-UHFFFAOYSA-N benzene;n,n-dimethylformamide Chemical compound CN(C)C=O.C1=CC=CC=C1 NHVHYFAWHCJELN-UHFFFAOYSA-N 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 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 5
- 125000005059 halophenyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- 230000002378 acidificating effect Effects 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
- 238000006049 ring expansion reaction Methods 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003610 charcoal Substances 0.000 claims description 3
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 150000004967 organic peroxy acids Chemical class 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- XETNDXJRODUNHT-UHFFFAOYSA-N ethyl 2-(2-methyl-3-oxo-1,3-oxathiolan-2-yl)acetate Chemical compound CCOC(=O)CC1(C)OCCS1=O XETNDXJRODUNHT-UHFFFAOYSA-N 0.000 claims description 2
- KKYMKMYKHKCCOG-UHFFFAOYSA-N ethyl 6-methyl-2,3-dihydro-1,4-oxathiine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)OCCS1 KKYMKMYKHKCCOG-UHFFFAOYSA-N 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 claims description 2
- 238000004809 thin layer chromatography Methods 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- ODQRPTODALTOCU-UHFFFAOYSA-N 6-methyl-2,3-dihydro-1,4-oxathiine-5-carboxamide Chemical class CC1=C(C(N)=O)SCCO1 ODQRPTODALTOCU-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 2
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- AOOLFYMBFIGYDE-UHFFFAOYSA-N 2-chloro-3-oxobutanamide Chemical compound CC(=O)C(Cl)C(N)=O AOOLFYMBFIGYDE-UHFFFAOYSA-N 0.000 description 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 229940125890 compound Ia Drugs 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- GJRZXAUPJGXYBA-UHFFFAOYSA-N ethyl 2-(2-methyl-1,3-oxathiolan-2-yl)acetate Chemical compound CCOC(=O)CC1(C)OCCS1 GJRZXAUPJGXYBA-UHFFFAOYSA-N 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- DSXFPRKPFJRPIB-UHFFFAOYSA-N thiolan-3-one Chemical compound O=C1CCSC1 DSXFPRKPFJRPIB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA277,860A CA1036167A (en) | 1977-05-06 | 1977-05-06 | Process for preparing 5,6-dihydro-2-methyl-1,4-oxathiin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1594450A true GB1594450A (en) | 1981-07-30 |
Family
ID=4108593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17940/78A Expired GB1594450A (en) | 1977-05-06 | 1978-05-05 | 1,3-oxathiolane sulphoxides and their use in the preparation of 5,6-dihydro-2-methyl-1,4-oxathiin derivatives |
Country Status (6)
| Country | Link |
|---|---|
| JP (2) | JPS6016954B2 (enrdf_load_stackoverflow) |
| AU (1) | AU516809B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1036167A (enrdf_load_stackoverflow) |
| FR (2) | FR2401150B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1594450A (enrdf_load_stackoverflow) |
| IN (1) | IN148905B (enrdf_load_stackoverflow) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4189435A (en) * | 1977-05-06 | 1980-02-19 | Lee Wha S | Process for preparing 5,6-dihydro-2-methyl-1,4-oxathiin derivatives |
| CA1124248A (en) * | 1978-08-27 | 1982-05-25 | Andrew A. Znotins | Method of making 5,6-dihydro-2-methyl-n-phenyl-1,4- oxathiin-3-carboxamide |
| IL58177A (en) * | 1978-08-27 | 1984-08-31 | Uniroyal Ltd | Method of making 5,6-dihydro-2-methyl-n-phenyl-1,4-oxathiin-3-carboxamide |
| CA1109073A (en) * | 1978-09-05 | 1981-09-15 | Uniroyal Chemical Co./Uniroyal Chemical Cie. | Method of making 5,6-dihydro-2-methyl-n-phenyl-1,4- oxathiin-3-carboxamide |
| US4182716A (en) * | 1978-09-05 | 1980-01-08 | Uniroyal, Ltd. | Method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide |
| CA1166262A (en) * | 1981-08-11 | 1984-04-24 | Frederick M.M. Hager | Synthesis of intermediate for the manufacture of 5,6- dihydro-2-methyl-n-phenyl-1,4-oxathiin-3-carboxamide |
| JPS5922547A (ja) * | 1982-07-28 | 1984-02-04 | 富士電機株式会社 | 医療用ベツドの制御装置 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5010597A (enrdf_load_stackoverflow) * | 1973-05-25 | 1975-02-03 |
-
1977
- 1977-05-06 CA CA277,860A patent/CA1036167A/en not_active Expired
-
1978
- 1978-05-03 IN IN323/DEL/78A patent/IN148905B/en unknown
- 1978-05-05 FR FR7814495A patent/FR2401150B1/fr not_active Expired
- 1978-05-05 AU AU35837/78A patent/AU516809B2/en not_active Expired
- 1978-05-05 GB GB17940/78A patent/GB1594450A/en not_active Expired
- 1978-05-06 JP JP53054007A patent/JPS6016954B2/ja not_active Expired
- 1978-09-15 FR FR7827026A patent/FR2396010A1/fr active Granted
-
1982
- 1982-01-04 JP JP57000157A patent/JPS57131786A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2401150B1 (fr) | 1985-08-30 |
| CA1036167A (en) | 1978-08-08 |
| JPS6016954B2 (ja) | 1985-04-30 |
| JPS53149976A (en) | 1978-12-27 |
| FR2396010B1 (enrdf_load_stackoverflow) | 1985-02-22 |
| FR2396010A1 (fr) | 1979-01-26 |
| AU3583778A (en) | 1979-11-08 |
| FR2401150A1 (fr) | 1979-03-23 |
| AU516809B2 (en) | 1981-06-25 |
| JPS57131786A (en) | 1982-08-14 |
| IN148905B (enrdf_load_stackoverflow) | 1981-07-18 |
| JPS6135194B2 (enrdf_load_stackoverflow) | 1986-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |