Hydrochloric Acid → (4-phenyl-1,3-thiazol-2-yl)methanamine

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Reaktionsgleichung

Cl.[C:2]1([C:8]2[N:9]=[C:10]([CH2:13][NH:14]C(=O)C3C=CC=CC=3)[S:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.CO>O1CCOCC1>[C:2]1([C:8]2[N:9]=[C:10]([CH2:13][NH2:14])[S:11][CH:12]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

6N HCl (4.5 mL) was added to a solution of N-((4-phenylthiazol-2-yl)methyl)benzamide (150 mg, 0.51 mmol) in dioxane (10 mL) and the reaction mixture was stirred at 100° C. for 24 h (reaction monitored by TLC, eluant CHCl3/MeOH). Reaction mixture was concentrated under reduced pressure and the residue was dissolved in water. The aqueous layer was washed twice with EtOAc. The pH of the aqueous layer was then adjusted to pH ˜9 using 10% NaHCO3 and the organic product was extracted with EtOAc. The organic layer was washed with brine and concentrated under reduced pressure to yield (4-phenylthiazol-2-yl)methanamine (75 mg, yield 77%) as orange colored liquid, which was carried through without further purification. 1H NMR (300 MHz, CDCl3) δ 7.91-7.88 (m, 2H), 7.45-7.40 (m, 3H), 7.36-7.31 (m, 1H), 4.25 (br s, 2H), 3.79-3.75 (m, 1H), 3.68-3.63 (m, 1H). MS (ESI) m/z: Calculated for C10H10N2S: 190.06. found: 191.2 (M+H)+.

Aufarbeitung

customReaction mixture
concentrationwas concentrated under reduced pressure
dissolutionthe residue was dissolved in water
washThe aqueous layer was washed twice with EtOAc
extractionthe organic product was extracted with EtOAc
washThe organic layer was washed with brine
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-aa79831c87de449586f75271d309d1ee
Quelldatensatz: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08901156B2

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