2-Bromoaniline → HCID 18350678, Verbindung

HRID 430512

Reaktionsgleichung

[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9]([NH:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[C:18](O)=[O:19])(=O)[CH3:10].P(Cl)(Cl)Cl>N1C=CC=CC=1>[CH3:10][C:9]1[N:4]([C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[Br:1])[C:18](=[O:19])[C:14]2[S:15][CH:16]=[CH:17][C:13]=2[N:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: 105 °C

Versuchsvorschrift

To a mixture of pyridine (6 mL), 2-bromoaniline (1.03 g, 6 mmol), and 3-acetamidothiophene-2-carboxylic acid (0.555 g, 3 mmol) was added phosphorus trichloride (0.03 mL, 3.45 mmol). The reaction was heated to 105° C. for 4 hours, cooled to ambient temperature and partitioned between chloroform and water (an insoluble precipitate was removed by filtration). Phases were separated and the aqueous layer was extracted with chloroform. The combined organic phase was washed with water and brine, dried over magnesium sulfate and concentrated to a dull yellow film. This residue was flash chromatographed on silica gel (30×125 mm) eluting with 15-25% ethyl acetate/hexane to afford 0.411 g (47%) of 2-methyl-3-(2-bromophenyl)-3H-thieno[3,2-d]pyrimidin-4-one as a yellow foam,

Aufarbeitung

temperaturecooled to ambient temperature
custompartitioned between chloroform and water (an insoluble precipitate
customwas removed by filtration)
customPhases were separated
extractionthe aqueous layer was extracted with chloroform
washThe combined organic phase was washed with water and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated to a dull yellow film
customchromatographed on silica gel (30×125 mm)
washeluting with 15-25% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag: ord-b2bbe11e0c4f44b1a03d598b2dc6143b
Quelldatensatz: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06323208B1

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