Sodium Hydroxide → 2,4-Dichloro-7-(6,6-dimethyl-3,5,6,7-tetrahydropyrrolo-[2,1-c][1,2,4]thiadiazol-3-ylidenamino)-6-fluorobenzothiazole

HRID 21729

Reaktionsgleichung

[Cl:1][C:2]1[S:3][C:4]2[C:10]([N:11]=[C:12]=[S:13])=[C:9]([F:14])[CH:8]=[C:7]([Cl:15])[C:5]=2[N:6]=1.Cl.[NH2:17][C:18]1[NH:19][CH2:20][C:21]([CH3:24])([CH3:23])[CH:22]=1.[OH-].[Na+].BrBr>ClCCl.O>[Cl:1][C:2]1[S:3][C:4]2[C:10]([N:11]=[C:12]3[S:13][N:17]=[C:18]4[CH2:22][C:21]([CH3:24])([CH3:23])[CH2:20][N:19]34)=[C:9]([F:14])[CH:8]=[C:7]([Cl:15])[C:5]=2[N:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 2 °C

Versuchsvorschrift

A solution of 2 g 2,4-dichloro-6-fluoro-7-isothiocyanatobenzothiazole in 10 ml dichloromethane was added, dropwise, at 0° C., to a suspension of 1.1 g 2-amino-4,4-dimethylpyrroline hydrochloride in 20 ml dichloromethane. A solution of 0.3 g sodium hydroxide and 6 ml water was added, dropwise, at 2° C. to this mixture which was stirred for 3 hours, whereby the temperature rose to 20° C. The mixture was cooled to -10° C. and a solution of 1 g bromine in 10 ml dichloromethane was added, dropwise, slowly and the mixture stirred for I hour whereby the temperature rose to 10° C. The solution was washed with water and with dilute caustic soda, dried over magnesium sulfate and concentrated. The residue was recrystallised from diisopropyl ether. Yield: 1.5 g=53% of theory m.p.: 134°-136° C.

Aufarbeitung

customrose to 20° C
temperatureThe mixture was cooled to -10° C.
stirringdropwise, slowly and the mixture stirred for I hour whereby the temperature
customrose to 10° C
washThe solution was washed with water and with dilute caustic soda
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was recrystallised from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag: ord-d804bd441201440e948ae6abc9e51e2d
Quelldatensatz: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05424443

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