GB1369917A - Production of 2,1,3-benzothiadiazin-4-one-2,2-dioxides - Google Patents
Production of 2,1,3-benzothiadiazin-4-one-2,2-dioxidesInfo
- Publication number
- GB1369917A GB1369917A GB552572A GB552572A GB1369917A GB 1369917 A GB1369917 A GB 1369917A GB 552572 A GB552572 A GB 552572A GB 552572 A GB552572 A GB 552572A GB 1369917 A GB1369917 A GB 1369917A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- phosgene
- benzothiadiazin
- dioxides
- feb
- 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
- MQZXGMYANOJYIY-UHFFFAOYSA-N 2,2-dioxo-1h-2$l^{6},1,3-benzothiadiazin-4-one Chemical class C1=CC=C2C(=O)NS(=O)(=O)NC2=C1 MQZXGMYANOJYIY-UHFFFAOYSA-N 0.000 title abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 2
- -1 N,N-disubstituted carboxamide Chemical class 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 abstract 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 abstract 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 abstract 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000003495 polar organic solvent Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011814 protection agent Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 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
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2105687A DE2105687C2 (de) | 1971-02-08 | 1971-02-08 | Verfahren zur Herstellung von 3-substituierten 2,1,3-Benzothiadiazin-4-on-2,2-dioxiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1369917A true GB1369917A (en) | 1974-10-09 |
Family
ID=5798039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB552572A Expired GB1369917A (en) | 1971-02-08 | 1972-02-07 | Production of 2,1,3-benzothiadiazin-4-one-2,2-dioxides |
Country Status (9)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6130332A (en) * | 1994-05-10 | 2000-10-10 | Nissan Chemical Industries, Ltd. | Method of alkylating triazine derivatives |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3875155A (en) * | 1973-03-31 | 1975-04-01 | Basf Ag | Process for making salts of 3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide |
| DE2349114C2 (de) * | 1973-09-29 | 1985-11-14 | Basf Ag, 6700 Ludwigshafen | 3-sek.-Butyl-2,1,3-benzothiadiazin-(4)-on-2,2-dioxid |
| DE2357063C2 (de) * | 1973-11-15 | 1986-07-17 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von N-Isopropyl-2,1,3-benzothiadiazin-4-on-2,2-dioxid |
| US4051130A (en) * | 1974-08-15 | 1977-09-27 | The Dow Chemical Company | 4(3H)-oxobenzo-2,1,3-thiadiazine-2,2-dioxides and derivatives thereof |
| DE2458343A1 (de) * | 1974-12-10 | 1976-06-16 | Basf Ag | N-n'-disubstituierte 2,1,3-benzothiadiazin(4)on-2.2-dioxide |
| DE2553209C2 (de) * | 1975-11-27 | 1986-01-02 | Basf Ag, 6700 Ludwigshafen | 1-Methoxymethyl-3-isopropyl-2,1,3-benzothiadiazin(4)on-2,2-dioxid und diese enthaltende Herbizide |
| US4054440A (en) * | 1976-02-23 | 1977-10-18 | The Dow Chemical Company | 4(3H)-Oxobenzo-2,1,3-thiadiazine-2,2-dioxides |
| US4208514A (en) * | 1976-02-23 | 1980-06-17 | The Dow Chemical Company | 4(3H)-Oxobenzo-2,1,3-thiadiazine-2,2-dioxides |
| DE2710382C2 (de) * | 1977-03-10 | 1983-12-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 2,1,3-Benzothiadiazin-4-on-2,2-dioxid-derivaten |
| US4100281A (en) * | 1977-03-30 | 1978-07-11 | Fmc Corporation | Mono-5-substituted-thio-3-chloro-4H-1,2,6-thiadiazin-4-one antifungal agents |
| US4097594A (en) * | 1977-03-30 | 1978-06-27 | Fmc Corporation | Mono-5-substituted-3-chloro-4H-1,2,6-thiadiazin-4-one antifungal agents |
| US4139700A (en) * | 1977-07-27 | 1979-02-13 | Monsanto Company | Process for the preparation of bicyclothiadiazinones |
| DE2852274A1 (de) * | 1978-12-02 | 1980-06-19 | Basf Ag | Verfahren zur herstellung von sulfamidsaeurehalogeniden |
| DE2852159A1 (de) * | 1978-12-02 | 1980-06-19 | Basf Ag | Verfahren zur herstellung von amidosulfonsaeuren |
| DE3428837A1 (de) * | 1984-06-30 | 1986-01-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von n-phenyl(pyridyl)-sulfonyldiamiden |
| HU199815B (en) * | 1985-12-03 | 1990-03-28 | Nitrokemia Ipartelepek | Process for producing 3-isopropylbenzo-2-thia-1,3-diazinone-/4/2,2-dioxide |
| CN104447618A (zh) * | 2014-12-26 | 2015-03-25 | 合肥星宇化学有限责任公司 | 一种苯达松的纯化方法 |
| CN104557776A (zh) * | 2014-12-28 | 2015-04-29 | 江苏绿利来股份有限公司 | 灭草松的合成方法 |
| CN104693142B (zh) * | 2015-03-31 | 2016-11-23 | 中国石油大学(华东) | 一种改进苯达松生产方法 |
| CN111763184A (zh) * | 2020-07-18 | 2020-10-13 | 江苏省激素研究所股份有限公司 | 一种灭草松原药合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1120456B (de) * | 1958-10-01 | 1961-12-28 | Geigy Ag J R | Verfahren zur Herstellung von neuen 4-Oxo-3, 4-dihydro-2, 1, 3-benzothiadiazin-2, 2-dioxyden |
| BE702877A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1966-08-30 | 1968-02-21 |
-
1971
- 1971-02-08 DE DE2105687A patent/DE2105687C2/de not_active Expired
-
1972
- 1972-01-14 CH CH57472A patent/CH564546A5/xx not_active IP Right Cessation
- 1972-02-01 BE BE778819A patent/BE778819A/xx not_active IP Right Cessation
- 1972-02-03 US US00223341A patent/US3822257A/en not_active Expired - Lifetime
- 1972-02-04 FR FR7203809A patent/FR2126729A5/fr not_active Expired
- 1972-02-05 IT IT48155/72A patent/IT996046B/it active
- 1972-02-07 SU SU1744911A patent/SU509233A3/ru active
- 1972-02-07 GB GB552572A patent/GB1369917A/en not_active Expired
- 1972-02-08 JP JP7213380A patent/JPS5729470B1/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6130332A (en) * | 1994-05-10 | 2000-10-10 | Nissan Chemical Industries, Ltd. | Method of alkylating triazine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| BE778819A (fr) | 1972-08-01 |
| JPS5729470B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-06-23 |
| US3822257A (en) | 1974-07-02 |
| CH564546A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-31 |
| SU509233A3 (ru) | 1976-03-30 |
| FR2126729A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-10-06 |
| DE2105687C2 (de) | 1981-09-24 |
| DE2105687A1 (de) | 1972-09-07 |
| IT996046B (it) | 1975-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |