Sodium Azide → 1-(2-Azidoethoxy)-2-(2-methoxyethoxy)ethane

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])(=O)=O>>[N:1]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])=[N+:2]=[N-:3]

Participants

Reactant 2

HCID 33557Sodium Azide

HCID 126212722-(2-(2-Methoxyethoxy)ethoxy)ethyl methanesulfonate

Product 1

HCID 103752401-(2-Azidoethoxy)-2-(2-methoxyethoxy)ethane

Conditions

Temperature: 60 °C

Procedure

Sodium azide (5.37 g, 83 mmol) and 2-(2-(2-methoxyethoxy)ethoxy)ethyl methanesulfonate (20 g, 83 mmol) were added without solvent, the temperature was raised to 60° C. and the mixture stirred for 48 hours. The salts were filtered and ethyl acetate added to precipitate the dissolved salts and filtered again, producing 1-azido-2-(2-(2-methoxyethoxy)ethoxy)ethane.

Workup

filtrationThe salts were filtered
additionethyl acetate added
customto precipitate the dissolved salts
filtrationfiltered again

Sources & evidence

ORD record: ord-7dea1f94450c4aa0897b2f08013d7cef
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907105B1

Reaction notes

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