Diethyl 4-(bromomethyl)phenylphosphonate → 4-[[4-[Bis(2-hydroxyethyl)amino]phenyl]diazenyl]-1-[4-(diethoxyphosphoryl)benzyl]pyridinium bromide

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Reaction Conditions

Reaction Steps

A mixture of 4-[[4-[N,N-bis(hydroxylethyl)amino]phenyl]azo]pyridine (1) (0.286 g, 1.00 mmol, and 4-(bromomethyl)phenylphosphonate (2) (0.317 g, 1.00 mmol) was dissolved in CH2Cl2 (10 mL). The red mixture was heated under a nitrogen atmosphere at 60° C. for 4 h. The solvent was then removed under high vacuum and the residue was dried under high vacuum overnight. 1H NMR (500 MHz, DMSO-d6): δ 9.07 (d, 2H, JH-H=6 Hz), 8.14 (d, 2H, JH-H=7 Hz), 7.90 (d, 2H, JH-H=9.5 Hz), 7.76-7.80 (m, 2H), 7.62-7.64 (m, 2H), 7.07 (d, 2H, JH-H=9.5 Hz), 5.88 (s, 2H), 4.95-4.97 (m, 2H), 3.99-4.03 (m, 4H), 3.99-4.03 (m, 4H), 3.66-3.72 (m, 8H), 1.22 (t, 3H). 31P NMR (400 MHz, DMSO-d6): δ −18.07 (s, 1P). High resolution EI-MS: Calculated for C26H34N4O5P+, 513.22744. Found, 513.22668.

Provenance & Evidence