Phenacyl bromide → HCID 723245, Verbindung

HRID 1397305Notizen

Reaktionsgleichung

[NH2:1][C:2](=[S:13])[CH2:3][NH:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O>CCO.CCOC(C)=O>[C:18]1([C:16]2[N:1]=[C:2]([CH2:3][NH:4][C:5](=[O:12])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:13][CH:15]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of N-(2-amino-2-thioxoethyl)benzamide (300 mg, 1.54 mmol) and 2-bromoacetophenone (305 mg, 1.54 mmol) in EtOH (10 mL) was heated to 80° C. for 2 h. The reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The concentrated reaction mixture was diluted with EtOAc and the organic layer was washed with H2O and brine, and concentrated under reduced pressure to yield N-((4-phenylthiazol-2-yl)methyl)benzamide (0.4 g, yield 88%) as a white solid, which was carried through without further purification. 1H NMR (400 MHz, CDCl3) δ 8.69 (br s, 1H), 8.04-8.01 (dd, J=7.8 Hz, 1.5 Hz, 2H), 7.99-7.97 (m, 2H), 7.64 (s, 1H), 7.56-7.52 (m, 4H), 7.48-7.44 (m, 2H), 5.34 (d, J=6 Hz, 2H). MS (ESI) m/z: Calculated for C17H14N2OS: 294.08. found: 295.0 (M+H)+.

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
customthe solvent was evaporated under reduced pressure
customThe concentrated reaction mixture
washthe organic layer was washed with H2O and brine
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-05364d0b2daa4ebe822485ced9605b55
Quelldatensatz: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08901156B2

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