N-bromobutanimide → 8-(5-Bromo-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile
Reaktionsgleichung
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1([C:16]#[N:17])[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1.[Br:18]N1C(=O)CCC1=O>CN(C=O)C>[Br:18][C:5]1[S:1][C:2]([C:6]2([C:16]#[N:17])[CH2:7][CH2:8][C:9]3([O:13][CH2:12][CH2:11][O:10]3)[CH2:14][CH2:15]2)=[N:3][CH:4]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To a solution of 8-(1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile (1.78 g, 7.11 mmol) in anhydrous DMF (25 ml) was added N-bromosuccinimide (1.52 g, 8.53 mmol). The solution was heated at 50° C. for 2 h. The reaction was cooled to 23° C. then diluted with saturated aqueous NaS2O3 (175 ml) and extracted with EtOAc (2×130 ml). The combined organic layers were washed with brine (150 ml), dried over Na2SO4, filtered and concentrated. The crude yellow oil was purified via flash column chromatography (SiO2: 100% Hex to 60:40 Hex:EtOAc), to afford 8-(5-bromo-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile (1.43 g, 4.13 mmol, 58% yield) as an off-white solid. MS ESI: [M+H]+ m/z 331.1. 1H NMR (500 MHz, CDCl3): δ 7.66 (s, 1H), 4.01-3.93 (m, 4H), 2.39-2.26 (m, 4H), 2.07-2.01 (m, 2H), 1.88-1.86 (m, 2H).
Aufarbeitung
- temperatureThe reaction was cooled to 23° C.
- extractionextracted with EtOAc (2×130 ml)
- washThe combined organic layers were washed with brine (150 ml)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude yellow oil was purified via flash column chromatography (SiO2: 100% Hex to 60:40 Hex:EtOAc)
Quellen und Nachweise
- ORD-Eintrag
- ord-60cedf1f3a83412cbef9ad1848245cba
- Quelldatensatz
- uspto-grants-2013_10
- Patentnummer
- US08551984B2
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