GB953519A - A process for the production of dithiazine compounds - Google Patents
A process for the production of dithiazine compoundsInfo
- Publication number
- GB953519A GB953519A GB43467/62A GB4346762A GB953519A GB 953519 A GB953519 A GB 953519A GB 43467/62 A GB43467/62 A GB 43467/62A GB 4346762 A GB4346762 A GB 4346762A GB 953519 A GB953519 A GB 953519A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formaldehyde
- acid
- dihydro
- compound
- dithiazinyl
- 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
- MNQDKWZEUULFPX-UHFFFAOYSA-M dithiazanine iodide Chemical class [I-].S1C2=CC=CC=C2[N+](CC)=C1C=CC=CC=C1N(CC)C2=CC=CC=C2S1 MNQDKWZEUULFPX-UHFFFAOYSA-M 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 239000012670 alkaline solution Substances 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 235000019260 propionic acid Nutrition 0.000 abstract 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 abstract 1
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 abstract 1
- HRFHUAKPOBBRGE-UHFFFAOYSA-N 2-(4H-1,3,5-dithiazin-4-yl)acetic acid Chemical compound N=1C(SCSC1)CC(=O)O HRFHUAKPOBBRGE-UHFFFAOYSA-N 0.000 abstract 1
- QMWSBGCIPZEDPP-UHFFFAOYSA-N 5-methyl-1,3,5-dithiazinane Chemical compound CN1CSCSC1 QMWSBGCIPZEDPP-UHFFFAOYSA-N 0.000 abstract 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 abstract 1
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004471 Glycine Substances 0.000 abstract 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 abstract 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 abstract 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 abstract 1
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 abstract 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 235000004279 alanine Nutrition 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 235000009582 asparagine Nutrition 0.000 abstract 1
- 229960001230 asparagine Drugs 0.000 abstract 1
- -1 b -alanine Chemical compound 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 abstract 1
- 235000013922 glutamic acid Nutrition 0.000 abstract 1
- 239000004220 glutamic acid Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 235000004400 serine Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED37789A DE1162841B (de) | 1961-12-29 | 1961-12-29 | Verfahren zur Herstellung von Dihydro-1, 3, 5-dithiazinverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB953519A true GB953519A (en) | 1964-03-25 |
Family
ID=7043777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB43467/62A Expired GB953519A (en) | 1961-12-29 | 1962-11-16 | A process for the production of dithiazine compounds |
Country Status (6)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4200741A (en) * | 1978-11-17 | 1980-04-29 | International Flavors & Fragrances Inc. | Use of crystalline pure or substantially pure 2,4,6-tri-isobutyl-1,3,5-dithiazine and process for preparing same |
| US4228278A (en) | 1978-11-17 | 1980-10-14 | International Flavors & Fragrances Inc. | Preparation of 2,4,6-tri-isobutyl dihydro-1,3,5-dithiazine |
| US4647662A (en) * | 1984-12-22 | 1987-03-03 | Haarmann & Reimer Gmbh | Unsymmetrical dihydrodithiazines, and their use as fragrances and flavorings |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3326907A (en) * | 1964-04-30 | 1967-06-20 | Dow Chemical Co | Novel 6-halo-4-imino-1, 3, 5-dithiazine salts |
| RU2317987C1 (ru) * | 2006-06-01 | 2008-02-27 | Институт нефтехимии и катализа РАН | Способ получения 3-тиа-1,5-диазабицикло[3.2.1]октана или 6-метил-3-тиа-1,5-диазабицикло[3.2.1]октана или 5-[2-[1,3,5-дитиазинан-5-ил]-1-метилэтил]1,3,5-дитиазинана |
| RU2443693C1 (ru) * | 2010-06-29 | 2012-02-27 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | Способ получения 2- и 4-(1,3,5-дитиазинан-5-ил)-фенолов |
| RU2566374C2 (ru) * | 2010-08-05 | 2015-10-27 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | Способ получения 2- и 4-(1,3,5-дитиазинан-5-ил)-фенолов |
| RU2478623C2 (ru) * | 2011-05-30 | 2013-04-10 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | Способ получения (1,5,3-дитиазепинан-3-ил)(тио)фенолов |
| RU2478634C2 (ru) * | 2011-06-16 | 2013-04-10 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | СПОСОБ ПОЛУЧЕНИЯ α,ω-БИС-(1,5,3-ДИТИАЗЕПИНАН-3-ИЛ)АЛКАНОВ |
| RU2478624C2 (ru) * | 2011-06-29 | 2013-04-10 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | СПОСОБ ПОЛУЧЕНИЯ 3-(о-, м-, п-НИТРОФЕНИЛ)-1,5,3-ДИТИАЗЕПАНОВ |
| RU2478625C2 (ru) * | 2011-07-01 | 2013-04-10 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | СПОСОБ ПОЛУЧЕНИЯ 3-(м-, п-МЕТИЛФЕНИЛ)-1,5,3-ДИТИАЗЕПАНОВ |
| RU2518485C2 (ru) * | 2012-09-27 | 2014-06-10 | Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук | Способ селективного получения 3,3'-[метиленбис(1,4-фенилен)]-, 3,3'-[оксибис(1,4-фенилен)]- и 3,3'-(3,3'-диметоксибифенил-4,4'-диил)-бис-1,5,3-дитиазепинанов |
| RU2518482C2 (ru) * | 2012-09-27 | 2014-06-10 | Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук | СПОСОБ ПОЛУЧЕНИЯ 3, 3'-[ОКСА(ТИА)АЛКАН-альфа, омега-ДИИЛ]-БИC-1, 5, 3-ДИТИАЗЕПИНАНОВ |
| RU2547267C2 (ru) * | 2013-02-26 | 2015-04-10 | Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук | Способ получения 3,3'-(3,6-диоксаоктан-1,8-диил)бис-1,5,3-дитиазепинана и его применение в качестве средства с фунгицидной активностью |
| RU2591196C2 (ru) * | 2014-11-21 | 2016-07-10 | Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук | Способ получения n,n-бис-[(1,5,3-дитиазепан-3-ил)алкил]аминов |
| US11549050B2 (en) | 2016-06-27 | 2023-01-10 | Clariant International Ltd. | Amorphous dithiazine dissolution formulation and method for using the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2273664A (en) * | 1939-04-21 | 1942-02-17 | Du Pont | Pest control |
-
0
- NL NL286047D patent/NL286047A/xx unknown
- BE BE626704D patent/BE626704A/xx unknown
-
1961
- 1961-12-29 DE DED37789A patent/DE1162841B/de active Pending
-
1962
- 1962-11-01 CH CH1280862A patent/CH421967A/de unknown
- 1962-11-16 GB GB43467/62A patent/GB953519A/en not_active Expired
-
1964
- 1964-06-22 US US377047A patent/US3281417A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4200741A (en) * | 1978-11-17 | 1980-04-29 | International Flavors & Fragrances Inc. | Use of crystalline pure or substantially pure 2,4,6-tri-isobutyl-1,3,5-dithiazine and process for preparing same |
| US4228278A (en) | 1978-11-17 | 1980-10-14 | International Flavors & Fragrances Inc. | Preparation of 2,4,6-tri-isobutyl dihydro-1,3,5-dithiazine |
| US4647662A (en) * | 1984-12-22 | 1987-03-03 | Haarmann & Reimer Gmbh | Unsymmetrical dihydrodithiazines, and their use as fragrances and flavorings |
Also Published As
| Publication number | Publication date |
|---|---|
| NL286047A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| DE1162841B (de) | 1964-02-13 |
| BE626704A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| US3281417A (en) | 1966-10-25 |
| CH421967A (de) | 1966-10-15 |
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