SU1085508A3 - Способ получени 2,3-дигидро-1,4-дитиинов - Google Patents
Способ получени 2,3-дигидро-1,4-дитиинов Download PDFInfo
- Publication number
- SU1085508A3 SU1085508A3 SU813364684A SU3364684A SU1085508A3 SU 1085508 A3 SU1085508 A3 SU 1085508A3 SU 813364684 A SU813364684 A SU 813364684A SU 3364684 A SU3364684 A SU 3364684A SU 1085508 A3 SU1085508 A3 SU 1085508A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dihydro
- general formula
- hydrogen
- dithiol
- yield
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- FLVUYLNVCUGFGX-UHFFFAOYSA-N 2,3-dihydro-1,4-dithiine Chemical class C1CSC=CS1 FLVUYLNVCUGFGX-UHFFFAOYSA-N 0.000 title claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003377 acid catalyst Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 150000004662 dithiols Chemical class 0.000 claims description 4
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- PCGDBWLKAYKBTN-UHFFFAOYSA-N 1,2-dithiole Chemical class C1SSC=C1 PCGDBWLKAYKBTN-UHFFFAOYSA-N 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 23
- 239000003921 oil Substances 0.000 description 12
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 6
- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 3
- BVEYJWQCMOVMAR-UHFFFAOYSA-N 5-Hydroxy-4-octanone Chemical compound CCCC(O)C(=O)CCC BVEYJWQCMOVMAR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- -1 oxycarbonyl compound Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YGKHJWTVMIMEPQ-UHFFFAOYSA-N 1,2-propanedithiol Chemical compound CC(S)CS YGKHJWTVMIMEPQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NYNZQNWKBKUAII-KBXCAEBGSA-N (3s)-n-[5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxypyrrolidine-1-carboxamide Chemical compound C1[C@@H](O)CCN1C(=O)NC1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 NYNZQNWKBKUAII-KBXCAEBGSA-N 0.000 description 1
- LFTMJBWNOFFSRW-UHFFFAOYSA-N 1,2-Butanedithiol Chemical compound CCC(S)CS LFTMJBWNOFFSRW-UHFFFAOYSA-N 0.000 description 1
- AKAIWNDBVZJOAJ-UHFFFAOYSA-N 1,4-dithiine Chemical compound S1C=CSC=C1 AKAIWNDBVZJOAJ-UHFFFAOYSA-N 0.000 description 1
- QPSJWMYYAPGJPU-UHFFFAOYSA-N 2-decyl-5,6-diethyl-2,3-dihydro-1,4-dithiine Chemical compound CCCCCCCCCCC1CSC(CC)=C(CC)S1 QPSJWMYYAPGJPU-UHFFFAOYSA-N 0.000 description 1
- ZSYNOYIEMSXEPO-UHFFFAOYSA-N 2-ethyl-5,6-dipropyl-2,3-dihydro-1,4-dithiine Chemical compound CCCC1=C(CCC)SC(CC)CS1 ZSYNOYIEMSXEPO-UHFFFAOYSA-N 0.000 description 1
- ODZTXUXIYGJLMC-UHFFFAOYSA-N 2-hydroxycyclohexan-1-one Chemical compound OC1CCCCC1=O ODZTXUXIYGJLMC-UHFFFAOYSA-N 0.000 description 1
- JPCDZLVTRNMSRK-UHFFFAOYSA-N 2-methyl-2,3-dihydro-1,4-dithiine Chemical compound CC1SC=CSC1 JPCDZLVTRNMSRK-UHFFFAOYSA-N 0.000 description 1
- ABBZAFKMTJQVSR-UHFFFAOYSA-N 2-methyl-5,6-dipropyl-2,3-dihydro-1,4-dithiine Chemical compound CCCC1=C(CCC)SC(C)CS1 ABBZAFKMTJQVSR-UHFFFAOYSA-N 0.000 description 1
- RJJRTZGKSVBEEK-UHFFFAOYSA-N 3-propoxypropane-1,2-dithiol Chemical compound CCCOCC(S)CS RJJRTZGKSVBEEK-UHFFFAOYSA-N 0.000 description 1
- UXHQLGLGLZKHTC-CUNXSJBXSA-N 4-[(3s,3ar)-3-cyclopentyl-7-(4-hydroxypiperidine-1-carbonyl)-3,3a,4,5-tetrahydropyrazolo[3,4-f]quinolin-2-yl]-2-chlorobenzonitrile Chemical compound C1CC(O)CCN1C(=O)C1=CC=C(C=2[C@@H]([C@H](C3CCCC3)N(N=2)C=2C=C(Cl)C(C#N)=CC=2)CC2)C2=N1 UXHQLGLGLZKHTC-CUNXSJBXSA-N 0.000 description 1
- OVBZTVYBXDWHAA-UHFFFAOYSA-N 4-hydroxyhexan-3-one Chemical compound CCC(O)C(=O)CC.CCC(O)C(=O)CC OVBZTVYBXDWHAA-UHFFFAOYSA-N 0.000 description 1
- SKCYVGUCBRYGTE-UHFFFAOYSA-N 4-hydroxyhexan-3-one Chemical compound CCC(O)C(=O)CC SKCYVGUCBRYGTE-UHFFFAOYSA-N 0.000 description 1
- ZZVIQKZCYRVUSW-UHFFFAOYSA-N 5,6-dihexyl-2,3-dihydro-1,4-dithiine Chemical compound CCCCCCC1=C(CCCCCC)SCCS1 ZZVIQKZCYRVUSW-UHFFFAOYSA-N 0.000 description 1
- FAYLFGHUYPPDPQ-UHFFFAOYSA-N 5,6-dimethyl-2,3-dihydro-1,4-dithiine Chemical compound CC1=C(C)SCCS1 FAYLFGHUYPPDPQ-UHFFFAOYSA-N 0.000 description 1
- ODMMTPOMHVDNHF-UHFFFAOYSA-N 5,6-dipropyl-2,3-dihydro-1,4-dithiine Chemical compound CCCC1=C(CCC)SCCS1 ODMMTPOMHVDNHF-UHFFFAOYSA-N 0.000 description 1
- XRCNPRZPSUNYAI-UHFFFAOYSA-N 5-methyl-2,3-dihydro-1,4-dithiine Chemical compound CC1=CSCCS1 XRCNPRZPSUNYAI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 150000008119 dithiins Chemical class 0.000 description 1
- GWNVJSUBDMCUDB-UHFFFAOYSA-N dodecane-1,2-dithiol Chemical compound CCCCCCCCCCC(S)CS GWNVJSUBDMCUDB-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005283 haloketone group Chemical group 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000365995A CA1150284A (en) | 1980-12-02 | 1980-12-02 | Method of making certain 2,3-dihydro-1,4-dithiins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1085508A3 true SU1085508A3 (ru) | 1984-04-07 |
Family
ID=4118618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU813364684A SU1085508A3 (ru) | 1980-12-02 | 1981-12-01 | Способ получени 2,3-дигидро-1,4-дитиинов |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4319033A (en:Method) |
| EP (1) | EP0053494B1 (en:Method) |
| JP (1) | JPS57140782A (en:Method) |
| KR (1) | KR870000285B1 (en:Method) |
| AU (1) | AU548047B2 (en:Method) |
| BR (1) | BR8107821A (en:Method) |
| CA (1) | CA1150284A (en:Method) |
| DE (1) | DE3175599D1 (en:Method) |
| HU (1) | HU187479B (en:Method) |
| IL (1) | IL64412A (en:Method) |
| IN (1) | IN163673B (en:Method) |
| SU (1) | SU1085508A3 (en:Method) |
| YU (1) | YU280581A (en:Method) |
| ZA (1) | ZA818232B (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2574393C2 (ru) * | 2010-05-21 | 2016-02-10 | Байер Кропсайенс Аг | Способ синтеза дитиин-тетракарбокси-диимидов |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1186321A (en) * | 1982-05-06 | 1985-04-30 | Uniroyal, Ltd. | Method of synthesizing dihydro-1, 4-dithiins |
| US5580544A (en) * | 1995-03-29 | 1996-12-03 | Uniroyal Chemical Company, Inc. | Paste formulation useful for seed treatment and foliar treatment of plants |
| US5719103A (en) * | 1996-05-02 | 1998-02-17 | Uniroyal Chemical Company, Inc. | Powder formulation useful for seed treatment and foliar treatment of plants |
| US7081436B2 (en) | 2001-01-26 | 2006-07-25 | General Electric Company | Paste formulation for seed treatment of plants |
| JP4811573B2 (ja) * | 2003-10-31 | 2011-11-09 | 日産化学工業株式会社 | １，４−ジチイン環を有する化合物を含む電荷輸送性有機材料 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3920438A (en) * | 1973-05-07 | 1975-11-18 | Uniroyal Inc | Substituted dithin tetroxide plant growth regulants |
| US3947264A (en) * | 1974-04-09 | 1976-03-30 | Uniroyal, Inc. | Substituted 2,3-dihydro-,4-oxathiin plant growth stunting agents |
| US4004018A (en) * | 1974-06-20 | 1977-01-18 | Uniroyal Inc. | 2,3-Dihydro-1,4-dithiin 1,1,4,4-tetroxide antimicrobials |
| US4026906A (en) * | 1975-01-10 | 1977-05-31 | Uniroyal Inc. | Substituted dithiin tetroxide plant growth regulants |
-
1980
- 1980-12-02 CA CA000365995A patent/CA1150284A/en not_active Expired
-
1981
- 1981-03-26 US US06/247,670 patent/US4319033A/en not_active Expired - Lifetime
- 1981-11-26 IN IN745/DEL/81A patent/IN163673B/en unknown
- 1981-11-26 ZA ZA818232A patent/ZA818232B/xx unknown
- 1981-11-27 DE DE8181305614T patent/DE3175599D1/de not_active Expired
- 1981-11-27 EP EP81305614A patent/EP0053494B1/en not_active Expired
- 1981-11-30 AU AU78107/81A patent/AU548047B2/en not_active Expired
- 1981-12-01 SU SU813364684A patent/SU1085508A3/ru active
- 1981-12-01 BR BR8107821A patent/BR8107821A/pt unknown
- 1981-12-01 IL IL64412A patent/IL64412A/xx not_active IP Right Cessation
- 1981-12-01 KR KR1019810004667A patent/KR870000285B1/ko not_active Expired
- 1981-12-02 YU YU02805/81A patent/YU280581A/xx unknown
- 1981-12-02 HU HU813624A patent/HU187479B/hu unknown
- 1981-12-02 JP JP56194354A patent/JPS57140782A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| 1. Патент US 1 3920438, кл. 71-73, опублик. 1976 (прототип). * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2574393C2 (ru) * | 2010-05-21 | 2016-02-10 | Байер Кропсайенс Аг | Способ синтеза дитиин-тетракарбокси-диимидов |
| RU2574393C9 (ru) * | 2010-05-21 | 2016-10-10 | Байер Кропсайенс Аг | Способ синтеза дитиин-тетракарбокси-диимидов |
Also Published As
| Publication number | Publication date |
|---|---|
| KR830007621A (ko) | 1983-11-04 |
| IL64412A0 (en) | 1982-03-31 |
| EP0053494B1 (en) | 1986-11-12 |
| BR8107821A (pt) | 1982-09-08 |
| DE3175599D1 (en) | 1987-01-02 |
| US4319033A (en) | 1982-03-09 |
| AU7810781A (en) | 1982-06-10 |
| IN163673B (en:Method) | 1988-10-29 |
| IL64412A (en) | 1985-02-28 |
| YU280581A (en) | 1984-02-29 |
| JPS6228141B2 (en:Method) | 1987-06-18 |
| CA1150284A (en) | 1983-07-19 |
| KR870000285B1 (ko) | 1987-02-25 |
| JPS57140782A (en) | 1982-08-31 |
| ZA818232B (en) | 1983-04-27 |
| AU548047B2 (en) | 1985-11-21 |
| HU187479B (en) | 1986-01-28 |
| EP0053494A1 (en) | 1982-06-09 |
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