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

HRID 879092Notes

Reaction equation

[OH:1][CH2:2][CH2:3][N:4]([C:8]1[CH:13]=[CH:12][C:11]([N:14]=[N:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)[CH2:5][CH2:6][OH:7].[Br:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([P:30](=[O:37])([O:34][CH2:35][CH3:36])[O:31][CH2:32][CH3:33])=[CH:26][CH:25]=1>C(Cl)Cl>[Br-:22].[OH:7][CH2:6][CH2:5][N:4]([CH2:3][CH2:2][OH:1])[C:8]1[CH:9]=[CH:10][C:11]([N:14]=[N:15][C:16]2[CH:21]=[CH:20][N+:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([P:30]([O:34][CH2:35][CH3:36])([O:31][CH2:32][CH3:33])=[O:37])=[CH:26][CH:25]=3)=[CH:18][CH:17]=2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

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.

Workup

customThe solvent was then removed under high vacuum
customthe residue was dried under high vacuum overnight

Sources & evidence

ORD record: ord-c61a3c062b254ff6823449e07663cc73
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987710B2

Reaction notes

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