CS265777B1 - A process for preparing 6-bromo-2-benzothiazolinone - Google Patents
A process for preparing 6-bromo-2-benzothiazolinone Download PDFInfo
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- CS265777B1 CS265777B1 CS873464A CS346487A CS265777B1 CS 265777 B1 CS265777 B1 CS 265777B1 CS 873464 A CS873464 A CS 873464A CS 346487 A CS346487 A CS 346487A CS 265777 B1 CS265777 B1 CS 265777B1
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- benzothiazolinone
- bromo
- preparing
- bromosuccinimide
- chloroform
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- Thiazole And Isothizaole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Účelom riešenia je spůsob přípravy 6-bróm-2-benzotiazolinónu. Reakcia sa uskutočňuje bromáciou 2-benzotiazolinónu N-brómsukcínimidom v chloroforme. 6-bróm- -2-benzotiazolinón je rektívny medziprodukt pre syntézu herbicídov, fungioídov a bakterieídov.The purpose of the solution is the preparation method of 6-bromo-2-benzothiazolinone. The reaction is carried out by bromination of 2-benzothiazolinone with N-bromosuccinimide in chloroform. 6-Bromo-2-benzothiazolinone is a reactive intermediate for the synthesis of herbicides, fungicides and bacterioids.
Description
Uvedená zlúčenina bola připravená bromáciou 2-benzitiazolinónu resp. 2-chlórbenzotiazolu elementárnym brómom, diazotáciou a Sandmayerovou reakciou zo 6-amino-2-benzotiazolinónu (Colonna, Μ., Publ. Ist. Chim. Univ. Bologna, 1 943,3; C. A. 41, 754 g (1947).) a alkalickou hydrolýzou 2,6-dibrómbenzotiazolu (Elderfield, R. C., Short, F. W., J. Org. Chem. 181 092 (1953).).The title compound was prepared by bromination of 2-benzithiazolinone, respectively. 2-chlorobenzothiazole by elemental bromine, diazotization and a Sandmayer reaction from 6-amino-2-benzothiazolinone (Colonna, Μ., Publ. Ist. Chim. Univ. Bologna, 1943.3; CA 41, 754 g (1947)); and by alkaline hydrolysis of 2,6-dibromobenzothiazole (Elderfield, RC, Short, FW, J. Org. Chem. 181 092 (1953)).
Teraz bol zistený jednoduchý a bezpečný spósob přípravy uvedenej zlúčeniny, ktorý nevyžaduje manipuláoiu s elementárnym brómom a vyznačuje sa tým,.že sa nechá reagovat 2-benzotiazolinón s N-brómsukcínimidom v chloroforme za varu.It has now been found a simple and safe process for the preparation of said compound which does not require the manipulation of elemental bromine and is characterized by reacting 2-benzothiazolinone with N-bromosuccinimide in chloroform at boiling.
PřikladlEXAMPLE
Příprava 6-bróm-2benzotiazolinónuPreparation of 6-bromo-2-benzothiazolinone
K homogénnej zmesi práškovitého 2-benzotiažolinónu (15,1 g, 0,1 mol) a N-brómsukcínimidu (17,8 g, 0,1 mol) sa přidal chloroform (50 cm ) a reakčná zmes sa zahriala do varu. Po rozpuštění tuhého podielu sa reflux udržiaval ešte 5 minút, počas ktorej doby vypadával tuhý produkt. Po ochladnutí zmesi na teplotu miestnosti surový 6-bróm-2-benzotiazolinón sa odsál a premyl chloridom uhličitým.To a homogeneous mixture of powdery 2-benzothiazolinone (15.1 g, 0.1 mol) and N-bromosuccinimide (17.8 g, 0.1 mol) was added chloroform (50 cm) and the reaction mixture was heated to boiling. After dissolution of the solid, reflux was maintained for a further 5 minutes, during which time a solid product precipitated. After cooling the mixture to room temperature, the crude 6-bromo-2-benzothiazolinone was aspirated and washed with carbon tetrachloride.
Po vysušení sa produkt zahrial do varu s vodou (200 cm3) a ihned sa odsál a premyl studenou vodou. Získal sa surový 6-bróm-2-benzotiazolinón s t. t. 225 až 230 °C v množstve 17,1 g (73,4 %).After drying, the product was heated to boiling with water (200 cm 3 ) and immediately aspirated and washed with cold water. Crude 6-bromo-2-benzothiazolinone with mp 225-230 ° C was obtained in an amount of 17.1 g (73.4%).
Vzorka pre analýzu bola prekryštalizovaná z etanolu za použitia aktívneho uhlia, čím sa získal čistý 6-bróm-2-benzotiazolinčn s t. t. 229 až 231 °C. Literatúra udává 226 až 228 °C (Colonna, Μ., Publ. Ist. Chim. Univ. Bologna, 1 943,3.; C. A. 41, 754 g (1947).A sample for analysis was recrystallized from ethanol using activated carbon to give pure 6-bromo-2-benzothiazolinone with m.p. t. Mp 229-231 ° C. The literature indicates 226-228 ° C (Colonna, Μ., Publ. Ist. Chim. Univ. Bologna, 1943.3 .; C.A. 41, 754 g (1947)).
Pre C^H^BrNOS (230,09) vypočítané %: C 36,54 H 1,75 N 6,09 S 13,93 Br 34,73 zistené %: 36,27 1,63 5,9-5 13,91 34,75For C% HH ^ Br BrNOS (230.09) calculated%: C 36.54 H 1.75 N 6.09 S 13.93 Br 34.73 found%: 36.27 1.63 5.9-5 13, 91 34.75
6-bróm-2-benzotiazolinón, připravený podlá příkladu 1, sa používá ako reaktívny medziprodukt pre syntézu herbicídov (Lácová, Μ., Sidóová, Ε., Konečný, V., čs. AO 246 247 (1986)., D'Amico, J. J:, Us pat. 4 185 990 (1980),) a regulátorov rastu rastlín (Monsanto Co., Jap. pat. 79 151 996 (1979)., D'Amico, J. J., Eur. pat Appl. 7,772 (1980).), ako aj dalších zlúčenín s předpokládanou biologickou aktivitou.6-Bromo-2-benzothiazolinone, prepared according to Example 1, is used as a reactive intermediate for herbicide synthesis (Lácová, Sid., Sidóová, Ε., Konecny, V., AO 246 247 (1986)., D'Amico J. J., U.S. Pat. No. 4,185,990 (1980), and plant growth regulators (Monsanto Co., Jap. Pat. 79,115,996 (1979)., D'Amico, JJ, Eur. Appl. 7,772). (1980)), as well as other compounds with predicted biological activity.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS873464A CS265777B1 (en) | 1987-05-14 | 1987-05-14 | A process for preparing 6-bromo-2-benzothiazolinone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS873464A CS265777B1 (en) | 1987-05-14 | 1987-05-14 | A process for preparing 6-bromo-2-benzothiazolinone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS346487A1 CS346487A1 (en) | 1989-03-14 |
| CS265777B1 true CS265777B1 (en) | 1989-11-14 |
Family
ID=5374781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS873464A CS265777B1 (en) | 1987-05-14 | 1987-05-14 | A process for preparing 6-bromo-2-benzothiazolinone |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS265777B1 (en) |
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1987
- 1987-05-14 CS CS873464A patent/CS265777B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS346487A1 (en) | 1989-03-14 |
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