Dimethylformamide → 6-Bromo-2-chlorobenzothiazole

HRID 70136

Reaktionsgleichung

CN(C=O)C.P(Cl)(Cl)([Cl:8])=O.[Br:11][C:12]1[CH:21]=[CH:20][C:15]2[NH:16][C:17](=O)[S:18][C:14]=2[CH:13]=1.C([O-])([O-])=O.[K+].[K+]>O>[Br:11][C:12]1[CH:21]=[CH:20][C:15]2[N:16]=[C:17]([Cl:8])[S:18][C:14]=2[CH:13]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

DMF (0.807 mL, 10.4 mmol) was added to phosphorous oxychloride (8.10 mL, 86.9 mmol), and the reaction mixture was stirred for 15 min. 6-bromobenzo[d]thiazol-2(3H)-one (2.00 g, 8.69 mmol) was added and the reaction mixture was heated to 100° C. overnight. Upon cooling to rt, the reaction mixture was slowly added to a solution of K2CO3 (75 g) in water (200 mL) while maintaining the temperature below 35° C. Additional K2CO3 was added in order to maintain the pH above 10. Upon complete addition, the mixture was allowed to stir for 1 h. The solid was collected by filtration, washed with water (2×25 mL), and air dried. Further drying in a vacuum oven gave 2.06 g (95%) of the desired product as a brown solid. The material was used without further purification. LC-MS: RT=9.94 min., compound does not ionize.

Aufarbeitung

temperatureUpon cooling to rt
temperaturewhile maintaining the temperature below 35° C
temperatureto maintain the pH above 10
additionUpon complete addition
stirringto stir for 1 h
filtrationThe solid was collected by filtration
washwashed with water (2×25 mL), and air
customdried
customFurther drying in a vacuum oven

Quellen und Nachweise

ORD-Eintrag: ord-0cbfa0965f994ce7b31dbfe2762142bb
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08822472B2

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