Bromine → 5,7-Difluorobenzo[d]thiazol-2-amine

HRID 9570

Reaktionsgleichung

[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH2:12])=[S:11])[CH:5]=[C:6]([F:8])[CH:7]=1.BrBr>ClCCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]2[S:11][C:10]([NH2:12])=[N:9][C:4]=2[CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 10 °C

Versuchsvorschrift

To a suspension of N-(3,5-difluorophenyl) thiourea (3.40 g, 18.07 mmol) in DCE (95 mL) was added a solution of bromine in DCE (5 mL) below 30° C. The mixture was heated at reflux for 2.5 h, then cooled to 10° C., and the precipitate formed was collected by filtration and washed with DCE. The solid was stirred with water (200 mL), basified by treatment with conc. ammonium hydroxide, filtered, and dried in a vacuum oven to afford 5,7-difluoro-1,3-benzothiazol-2-amine (3.05 g, 90%). ret. time 2.18; m/z 187.1 (NH+); 1H NMR (400 MHz, DMSO-d6) δ 6.92 (m, 1H), 7.00 (m, 2H), 7.92 (s, 2H).

Aufarbeitung

temperatureThe mixture was heated
temperatureat reflux for 2.5 h
customthe precipitate formed
filtrationwas collected by filtration
washwashed with DCE
filtrationfiltered
customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag: ord-4f7aa1f4483046469aab193d0211f406
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07091228B2

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