4-Nitro-2-(trifluoromethyl)-1,3-benzoxazole → 2-(Trifluoromethyl)-4-benzoxazolamine

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Reaktionsgleichung

[N+:1]([C:4]1[C:9]2[N:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>CCOC(C)=O.[Fe]>[NH2:1][C:4]1[C:9]2[N:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

Compound 476A (10.75 g, 46.30 mmol) was dissolved in 1:1 EtOAc/10% HOAc (250 mL) and heated to 65° C. Iron powder (12.93 g, 231.5 mmol) was added portionwise and the reaction was stirred for 6 h at 65° C. After cooling, the mixture was filtered through Celite rinsing with EtOAc. The organic layer was separated, washed with H2O (3×100 mL), brine (100 mL), dried over MgSO4, and concentrated in vacuo to give a brown oil. The crude material was purified by flash chromatography on silica gel eluting with 70/30 CH2Cl2/hexanes to give compound 476B (7.02 g, 75%) as a yellow crystalline solid. HPLC: 96.7% at 2.68 min (retention time) (YMC S5 ODS column, 4.6×50 mm, eluting with 10-90% aqueous methanol over 4 mincontaining 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

Aufarbeitung

temperatureAfter cooling
filtrationthe mixture was filtered through Celite
washrinsing with EtOAc
customThe organic layer was separated
washwashed with H2O (3×100 mL), brine (100 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto give a brown oil
customThe crude material was purified by flash chromatography on silica gel eluting with 70/30 CH2Cl2/hexanes

Quellen und Nachweise

ORD-Eintrag: ord-b44d3388ad714dc98221e1b5a5490271
Quelldatensatz: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07470797B2

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