CA1065320A - Preparation of 2-(3-methylpiperidinothio)-benzothiazole and 2-(4-methylpiperidinothio)-benzothiazole - Google Patents
Preparation of 2-(3-methylpiperidinothio)-benzothiazole and 2-(4-methylpiperidinothio)-benzothiazoleInfo
- Publication number
- CA1065320A CA1065320A CA233,629A CA233629A CA1065320A CA 1065320 A CA1065320 A CA 1065320A CA 233629 A CA233629 A CA 233629A CA 1065320 A CA1065320 A CA 1065320A
- Authority
- CA
- Canada
- Prior art keywords
- amine
- benzothiazole
- methylpiperidine
- methylpiperidinothio
- group
- 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
- JGCDEKLDKXSNJE-UHFFFAOYSA-N 2-(4-methylpiperidin-1-yl)sulfanyl-1,3-benzothiazole Chemical compound C1CC(C)CCN1SC1=NC2=CC=CC=C2S1 JGCDEKLDKXSNJE-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- GQXVNLBNGZXTGJ-UHFFFAOYSA-N 2-(3-methylpiperidin-1-yl)sulfanyl-1,3-benzothiazole Chemical compound C1C(C)CCCN1SC1=NC2=CC=CC=C2S1 GQXVNLBNGZXTGJ-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 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 abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 239000012266 salt solution Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- 239000007844 bleaching agent Substances 0.000 claims description 22
- 239000002002 slurry Substances 0.000 claims description 12
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 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 9
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 claims description 8
- -1 amine salt Chemical class 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000000376 reactant Substances 0.000 abstract description 7
- 239000007800 oxidant agent Substances 0.000 abstract description 2
- 239000008187 granular material Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- OEZWWCFLLFPENR-UHFFFAOYSA-N 3-methylpiperidin-1-ium;sulfate Chemical compound [O-]S([O-])(=O)=O.CC1CCC[NH2+]C1.CC1CCC[NH2+]C1 OEZWWCFLLFPENR-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- CVLWYOPXQNDTMC-UHFFFAOYSA-N acetic acid;4-methylpiperidine Chemical compound CC(O)=O.CC1CCNCC1 CVLWYOPXQNDTMC-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- DNHGDLPVASJBDU-UHFFFAOYSA-N 3-methylpiperidin-1-ium;phosphate Chemical compound [O-]P([O-])([O-])=O.CC1CCC[NH2+]C1.CC1CCC[NH2+]C1.CC1CCC[NH2+]C1 DNHGDLPVASJBDU-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- GHRWHEKMYXUOGO-UHFFFAOYSA-N 4-methylpiperidin-1-ium;chloride Chemical compound Cl.CC1CCNCC1 GHRWHEKMYXUOGO-UHFFFAOYSA-N 0.000 description 1
- TXLZADJSYQUVIJ-UHFFFAOYSA-N 4-methylpiperidin-1-ium;sulfate Chemical compound [O-]S([O-])(=O)=O.CC1CC[NH2+]CC1.CC1CC[NH2+]CC1 TXLZADJSYQUVIJ-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical group [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- VLDHWMAJBNWALQ-UHFFFAOYSA-M sodium;1,3-benzothiazol-3-ide-2-thione Chemical compound [Na+].C1=CC=C2SC([S-])=NC2=C1 VLDHWMAJBNWALQ-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002311 subsequent effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
- C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
- C08K5/47—Thiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51280674A | 1974-10-04 | 1974-10-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1065320A true CA1065320A (en) | 1979-10-30 |
Family
ID=24040650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA233,629A Expired CA1065320A (en) | 1974-10-04 | 1975-08-18 | Preparation of 2-(3-methylpiperidinothio)-benzothiazole and 2-(4-methylpiperidinothio)-benzothiazole |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5159871A (OSRAM) |
| BE (1) | BE833693A (OSRAM) |
| BR (1) | BR7506358A (OSRAM) |
| CA (1) | CA1065320A (OSRAM) |
| DE (1) | DE2537755A1 (OSRAM) |
| FR (1) | FR2286828A1 (OSRAM) |
| GB (1) | GB1464338A (OSRAM) |
| NL (1) | NL7511675A (OSRAM) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1050998B (de) * | 1954-07-27 | 1959-02-19 | United States Rubber Company, New York, N. Y. (V. St. A.) | Vulkanisationsverfahren für Kautschuk |
| GB1289654A (OSRAM) * | 1970-01-30 | 1972-09-20 |
-
1975
- 1975-05-14 GB GB2036475A patent/GB1464338A/en not_active Expired
- 1975-08-18 CA CA233,629A patent/CA1065320A/en not_active Expired
- 1975-08-25 DE DE19752537755 patent/DE2537755A1/de active Pending
- 1975-09-18 FR FR7528592A patent/FR2286828A1/fr active Granted
- 1975-09-22 BE BE160270A patent/BE833693A/xx unknown
- 1975-09-30 JP JP50118202A patent/JPS5159871A/ja active Pending
- 1975-10-01 BR BR7506358*A patent/BR7506358A/pt unknown
- 1975-10-03 NL NL7511675A patent/NL7511675A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7511675A (nl) | 1976-04-06 |
| JPS5159871A (en) | 1976-05-25 |
| BE833693A (fr) | 1976-01-16 |
| FR2286828A1 (fr) | 1976-04-30 |
| FR2286828B1 (OSRAM) | 1979-03-16 |
| GB1464338A (en) | 1977-02-09 |
| BR7506358A (pt) | 1976-08-17 |
| DE2537755A1 (de) | 1976-04-15 |
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