4-Benzeneazodiphenylamine → HCID 86747081, Verbindung

HRID 2253917

Reaktionsgleichung

C([Li])CCC.O[CH2:7][CH2:8][CH:9]1[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10]1.C1C=CC(NC2C=CC(N=NC3C=CC=CC=3)=CC=2)=CC=1.[CH3:37][N:38]([CH2:43][CH2:44][Br:45])[P:39](Cl)([Cl:41])=[O:40]>C1COCC1>[CH3:14][C:11]1([CH3:15])[O:10][CH:9]([CH2:8][CH2:7][P:39]([Cl:41])([N:38]([CH3:37])[CH2:43][CH2:44][Br:45])=[O:40])[CH2:13][O:12]1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

Butyllithium (10.8 ml, 21.60 mmol, 2.0M) was added dropwise at 0° C. to a stirred solution of 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (2.87 g, 19.60 mmol) and a crystal of 4-phenylazodiphenylamine indicator in THF (7 ml) under N2. The resulting solution was added dropwise at -78° C. to a stirred solution of N-methyl-N-(2-bromoethyl) phosphoramidic dichloride (5.00 g, 19.60 mmol) in THF (10 ml) under N2. The mixture was allowed to stir under N2 at -78° C. for 3 hr, at which time the purple mixture turned yellow. The mixture was warmed to room temperature and the solvent removed under reduced pressure. The residue was purified by chromatography (1:4 EtOAc: hexanes) and the product 16a isolated as an oil (4.77 g, 67%): Rf 0.61 (1:1 EtOAc:hexanes); 1H NMR (CDCl3) 4.26(dt, 2H, J= 8.44 Hz), 4.17(t, 1H, J=6.53 Hz), 4.06(t, 1H, J=7.06 Hz), 3.54(t, 1H, J=7.10 Hz), 3.44(m, 4H), 2.76(d, 3H, J=12.76 Hz), 1.95(dt, 2H, J=6.24 Hz), 1.67(d, 6H, 15.63 Hz); 31P NMR (CDCl3) -8.07 ppm.

Aufarbeitung

temperatureThe mixture was warmed to room temperature
customthe solvent removed under reduced pressure
customThe residue was purified by chromatography (1:4 EtOAc: hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-1584e8fa79314ef18ad20f7743f9285b
Quelldatensatz: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05233031

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