DD146707A5 - Verfahren zur herstellung von benzothiazolsulfenamiden - Google Patents
Verfahren zur herstellung von benzothiazolsulfenamiden Download PDFInfo
- Publication number
- DD146707A5 DD146707A5 DD79216364A DD21636479A DD146707A5 DD 146707 A5 DD146707 A5 DD 146707A5 DD 79216364 A DD79216364 A DD 79216364A DD 21636479 A DD21636479 A DD 21636479A DD 146707 A5 DD146707 A5 DD 146707A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- group
- reaction
- general formula
- temperature
- amine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- -1 BENZOTHIAZOLE SULFATE AMIDES Chemical class 0.000 title description 3
- 150000001412 amines Chemical class 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 15
- GPNLWUFFWOYKLP-UHFFFAOYSA-N s-(1,3-benzothiazol-2-yl)thiohydroxylamine Chemical class C1=CC=C2SC(SN)=NC2=C1 GPNLWUFFWOYKLP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 22
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 claims description 5
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 241000251730 Chondrichthyes Species 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- ILNGCUVXLQVDTC-UHFFFAOYSA-N 4-chloromorpholine Chemical compound ClN1CCOCC1 ILNGCUVXLQVDTC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- DLDIDQIZPBIVNQ-UHFFFAOYSA-N hydron;2-methylpropan-2-amine;chloride Chemical compound Cl.CC(C)(C)N DLDIDQIZPBIVNQ-UHFFFAOYSA-N 0.000 description 2
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 2
- XFFUBBGUJSBONN-UHFFFAOYSA-N n-chloro-2-methylpropan-2-amine Chemical compound CC(C)(C)NCl XFFUBBGUJSBONN-UHFFFAOYSA-N 0.000 description 2
- SJGFVFYSANQLLE-UHFFFAOYSA-N n-chlorocyclohexanamine Chemical compound ClNC1CCCCC1 SJGFVFYSANQLLE-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DQGBSPYYYCIELK-UHFFFAOYSA-N 1,1-bis(sulfanylidene)-1,3-benzothiazole Chemical compound C1=CC=C2S(=S)(=S)C=NC2=C1 DQGBSPYYYCIELK-UHFFFAOYSA-N 0.000 description 1
- HAAZMOAXEMIBAJ-UHFFFAOYSA-N 4-chloro-2-methylquinazoline Chemical compound C1=CC=CC2=NC(C)=NC(Cl)=C21 HAAZMOAXEMIBAJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/70—Sulfur atoms
- C07D277/76—Sulfur atoms attached to a second hetero atom
- C07D277/80—Sulfur atoms attached to a second hetero atom to a nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7830143A FR2439777A1 (fr) | 1978-10-24 | 1978-10-24 | Nouveau procede de preparation des benzothiazole-sulfenamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD146707A5 true DD146707A5 (de) | 1981-02-25 |
Family
ID=9214074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79216364A DD146707A5 (de) | 1978-10-24 | 1979-10-22 | Verfahren zur herstellung von benzothiazolsulfenamiden |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4252942A (cs) |
| EP (1) | EP0010477B1 (cs) |
| JP (1) | JPS5557577A (cs) |
| CA (1) | CA1121351A (cs) |
| CS (1) | CS213397B2 (cs) |
| DD (1) | DD146707A5 (cs) |
| DE (1) | DE2960495D1 (cs) |
| ES (1) | ES485304A1 (cs) |
| FR (1) | FR2439777A1 (cs) |
| SU (1) | SU961561A3 (cs) |
| YU (1) | YU258179A (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3517084A1 (de) * | 1985-05-11 | 1986-11-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von benzothiazolsulfenamiden |
| DE19500794A1 (de) * | 1995-01-13 | 1996-07-18 | Bayer Ag | Verfahren zur Herstellung von N,N-Dialkyl-, -Dicycloalkyl, -Diaryl- oder -Diaralkyl-benzthiazolyl-sulfenamiden |
| CN108727302A (zh) * | 2017-10-23 | 2018-11-02 | 科迈化工股份有限公司 | 一种环保型n-叔丁基-2-苯并噻唑次磺酰胺（ns）合成工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2782202A (en) * | 1955-09-27 | 1957-02-19 | Goodyear Tire & Rubber | Production of dry nu, nu-diisopropyl-2-benzothiazolesulfenamide |
| US2840556A (en) * | 1955-11-30 | 1958-06-24 | American Cyanamid Co | Preparation of sulfenmorpholides |
| US3161648A (en) * | 1963-04-11 | 1964-12-15 | American Cyanamid Co | Process for preparing nu, nu-diisopropylbenzothiazole-2-sulfenamide |
| US3658808A (en) * | 1968-01-02 | 1972-04-25 | American Cyanamid Co | Method of making 2-benzothiazole sulfenamides |
| BE754504A (fr) * | 1969-08-08 | 1971-02-08 | Bayer Ag | Procede pour la preparation de benzothiazylsulfenamides |
-
1978
- 1978-10-24 FR FR7830143A patent/FR2439777A1/fr active Granted
-
1979
- 1979-10-05 DE DE7979400707T patent/DE2960495D1/de not_active Expired
- 1979-10-05 US US06/082,206 patent/US4252942A/en not_active Expired - Lifetime
- 1979-10-05 EP EP79400707A patent/EP0010477B1/fr not_active Expired
- 1979-10-19 CA CA000338075A patent/CA1121351A/fr not_active Expired
- 1979-10-22 DD DD79216364A patent/DD146707A5/de unknown
- 1979-10-23 ES ES485304A patent/ES485304A1/es not_active Expired
- 1979-10-23 JP JP13694679A patent/JPS5557577A/ja active Pending
- 1979-10-23 SU SU792834363A patent/SU961561A3/ru active
- 1979-10-23 YU YU02581/79A patent/YU258179A/xx unknown
- 1979-10-24 CS CS797205A patent/CS213397B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES485304A1 (es) | 1980-05-16 |
| EP0010477A1 (fr) | 1980-04-30 |
| JPS5557577A (en) | 1980-04-28 |
| US4252942A (en) | 1981-02-24 |
| DE2960495D1 (en) | 1981-10-22 |
| YU258179A (en) | 1983-01-21 |
| CA1121351A (fr) | 1982-04-06 |
| EP0010477B1 (fr) | 1981-07-15 |
| CS213397B2 (en) | 1982-04-09 |
| FR2439777A1 (fr) | 1980-05-23 |
| SU961561A3 (ru) | 1982-09-23 |
| FR2439777B1 (cs) | 1981-05-29 |
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