CS265777B1 - SpAsob přípravy 6-bróm-2-benzotiazolinónu - Google Patents
SpAsob přípravy 6-bróm-2-benzotiazolinónu Download PDFInfo
- Publication number
- 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
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- benzothiazolinone
- bromo
- preparation
- bromosuccinimide
- boiling
- Prior art date
Links
- HECJMTPEVWQFCY-UHFFFAOYSA-N 6-bromo-3h-1,3-benzothiazol-2-one Chemical compound BrC1=CC=C2NC(=O)SC2=C1 HECJMTPEVWQFCY-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 8
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 claims description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 230000031709 bromination Effects 0.000 abstract description 2
- 238000005893 bromination reaction Methods 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 239000004009 herbicide Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- -1 2-benzothiazolinone N-bromosuccinimide Chemical compound 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LQVHXPZEBKDACR-UHFFFAOYSA-N 2,6-dibromo-1,3-benzothiazole Chemical compound C1=C(Br)C=C2SC(Br)=NC2=C1 LQVHXPZEBKDACR-UHFFFAOYSA-N 0.000 description 1
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 1
- CLYCLRFHPKKUBR-UHFFFAOYSA-N 6-amino-3h-1,3-benzothiazol-2-one Chemical compound NC1=CC=C2N=C(O)SC2=C1 CLYCLRFHPKKUBR-UHFFFAOYSA-N 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
Landscapes
- 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.
Description
Predmetom vynálezu je spůsob přípravy 6-bróm-2-benzotiazolinónu vzorca
Uvedená zlúčenina bola připravená bromáciou 2-benzitiazolinónu resp. 2-chlórbenzotiazolu elementárnym brómom, diazotáciou a Sandmayerovou reakciou zo 6-amino-2-benzotiazolinónu (Colonna, M., 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).).
Teraz bol zistený jednoduchý a bezpečný spdsob přípravy uvedenej zlúčeniny, ktorý nevyžaduje manipuláciu s elementárnym brómom a vyznačuje sa tým,.že sa nechá reagovat 2-benzotiazolinón s N-brómsukcínimidom v chloroforme za varu. Přikladl Příprava 6-bróm-2benzotiazolinónu K homogénnej zmesi práškovitého 2-benzotiažollnónu (15,1 g, 0,1 mol) a N-brómsukcínimidu 3 (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.
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 %).
Vzorka pre analýzu bola prekryštalizovaná z etanolu za použitia aktívneho uhlia, čím sa získal čistý 6-bróm-2-benzotiazolinón s t. t. 229 až 231 °C. Literatúre udává 226 až 228 °C (Colonna, M., Publ. Ist. Chim. Univ. Bologna, 1 943,3.; 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 34,75 6-bróm-2-benzotiazolinón, připravený podlá příkladu 1, sa používá ako reaktívny medziprodukt pre syntézu herbicídov (Lácová, M., Sidóová, E., 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 zlúčenin s předpokládanou biologickou aktivitou.
Claims (1)
- PREDMET VYNÁLEZU Spdsob přípravy 6-bróm-2-benzotiazolinónu vzorcavyznačujúci sa tým, že sa nechá reagovat 2-benzotiazolinón s ekvivalentným množstvom N-brómsukcínimidu v chloroforme za varu 2 až 15 minút.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS873464A CS265777B1 (cs) | 1987-05-14 | 1987-05-14 | SpAsob přípravy 6-bróm-2-benzotiazolinónu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS873464A CS265777B1 (cs) | 1987-05-14 | 1987-05-14 | SpAsob přípravy 6-bróm-2-benzotiazolinónu |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS346487A1 CS346487A1 (en) | 1989-03-14 |
| CS265777B1 true CS265777B1 (cs) | 1989-11-14 |
Family
ID=5374781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS873464A CS265777B1 (cs) | 1987-05-14 | 1987-05-14 | SpAsob přípravy 6-bróm-2-benzotiazolinónu |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS265777B1 (cs) |
-
1987
- 1987-05-14 CS CS873464A patent/CS265777B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS346487A1 (en) | 1989-03-14 |
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