ChemicalBook CAS DataBase List 2-Azidoethanol

2-Azidoethanol synthesis

5synthesis methods

Product Name:2-Azidoethanol
CAS Number:1517-05-1
Molecular formula:C2H5N3O
Molecular Weight:87.0806

2-Azidoethanol synthesis: Sodium azide (14.6 g, 224 mmol, 1.5 eq.) was added portion wise to a stirred mixture of 2- chloroethanol (12.0 g, 149 mmol, 1 eq.) in H2O (80 mL) at 0°C. The reaction mixture was slowly warmed up to room temperature and stirred for another 4 h. Additional sodium azide (9.71 g, 149 mmol, 1 eq.) was added and the solution was heated under reflux at 80°C overnight. After completion, the mixture was extracted with Et2O (3×50 mL) and the combined organic phases were washed with Brine (1× 10 mL) and dried over MgSO4. The solvent was removed in vacuo to yield a colorless oil (10.57 g, 121.4 mmol, 81%).
1 H NMR (400 MHz, CDCl3, ppm): δ=3.77 (q, 2H, CH2 OH), 3.43 (t, 2H, CH2 N3), 2.16 (s, 1H, OH). 13C NMR (101 MHz, CDCl3, ppm): δ=61.6 (CH2 OH), 53.7 (CH2 N3). 14N NMR (CDCl3, ppm): δ= 134 (Nβ), 171 (Nγ), 319 (Nα). C2H5N3O (87.08 gmol 1 ) calcd. N 48.25, C 27.59, H 5.79%; found IS: >40 J. FS: >360 N.

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Yield:1517-05-1 100%

Reaction Conditions:

with sodium azide in water at 80;Inert atmosphere;

Steps:

4.2.26 2-Azidoethan-1-ol
Sodium azide (4.68g, 72.0mmol, 3.0eq.) was weighted in a flask and was put under an atmosphere of nitrogen. Water (30mL, 0.8M) was added and then 2-bromoethanol (1.7mL, 24.01mmol, 1.0eq.). The mixture was stirred overnight at 80°C. The reaction solution was extracted with diethyl ether (4x). The combined organic layers were dried over anhydrous MgSO₄. Following filtration, the solvent was removed under reduced pressure to give 2-azidoethan-1-ol (2.091g, 100%) with R_f=0.37 (heptane:ethyl acetate 50:50) as a light-yellow oil. ¹H NMR (300MHz, CDCl₃): δ=3.79 (dd, J=10.0, 5.1Hz, 2H), 3.53 - 3.39 (m, 2H), 2.01 (t, J=5.6Hz, 1H) ppm. ¹³C NMR (75MHz, CDCl₃): δ=61.82, 53.83ppm.

References:

De Graef, Steff;De Ruysscher, Dries;Lescrinier, Eveline;Mattelaer, Charles-Alexandre;Nautiyal, Manesh;Pang, Luping;Rozenski, Jef;Strelkov, Sergei V.;Van Aerschot, Arthur;Weeks, Stephen D. [Bioorganic and medicinal chemistry,2020,vol. 28,# 15] Location in patent:supporting information

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42772-85-0 Synthesis