Hydrochloric Acid → (4-Azidophenyl)methanol

HRID 2404610Notes

Reaction equation

HRID 2404610 reaction equation
[N:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8]P(=C(C[N+](C)(C)C)O)=O)=[CH:6][CH:5]=1)=[N+:2]=[N-:3].NC1C=CC(C[OH:26])=CC=1.Cl.[N+]([O-])([O-])=O.[Na+].[N-]=[N+]=[N-].[Na+]>>[N:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][OH:26])=[CH:6][CH:5]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 24268Sodium NitrateHCID 33557Sodium AzideHCID 693314-Aminobenzyl alcoholHCID 178483607HCID 178483607, compound

Product 1

HCID 11171062(4-Azidophenyl)methanolYield 55%

Procedure

For example, 4-azidobenzylphosphorylcholine was made as follows: 4-aminobenzyl alcohol was treated with HCl and reacted with sodium nitrate, followed by sodium azide to yield 4-azidobenzyl alcohol. The product was recovered in 55% yield as a brown solid and purified by column chromatography. The product was characterized by NMR and IR. 4-azidobenzyl alcohol was treated with triethylamine, and 2-chloro-2-oxo-1,3,2-dioxaphospholane (COP) was added to the solution. The resulting compound was reacted with trimethylamine to yield the final product of 4-azidobenzylphosphorylcholine. The final product was obtained as a pale brown powder in 60% yield and characterized by NMR and IR.

Sources & evidence

ORD record
ord-ae3c66eb7d444598b864460096b3b863
Source dataset
uspto-grants-2014_08
Patent number
US08802738B2

Reaction notes

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