ChemicalBook CAS DataBase List 6-Azido-hexanoic acid

6-Azido-hexanoic acid synthesis

12synthesis methods

Product Name:6-Azido-hexanoic acid
CAS Number:79598-53-1
Molecular formula:C6H11N3O2
Molecular Weight:157

4224-62-8 Synthesis

4224-62-8
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79598-53-1
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172468-38-1
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Yield:79598-53-1 81%

Reaction Conditions:

with sodium azide in water;N,N-dimethyl-formamide

Steps:

1 Synthesis of 4-Azidobutyl Acetate (4.22)
Example 1
Synthesis of 4-Azidobutyl Acetate (4.22)
To a 500 mL flask was added 5.0 g (33 mmol, 1.0 eq) of 4-chlorobutylacetate and dissolved in 100 mL of DMF. Next 2.6 g (40 mmol, 1.2 eq) of sodium azide was added by a glass pipette.
A water condenser was placed onto the flask and the reaction heated to 80° C. for 16 hr with stirring.
The reaction was then cooled to room temperature and quenched with 300 mL of water to dissolve the sodium salts.
The aqueous solution was extracted with diethyl ether 3*100 mL.
The organic layers were combined and dried with MgSO₄.
The solution was filtered and concentrated under vacuum with no external heat, resulting in 4-azido-1-butylacetate (4.22), which was carried onto the next step without further purification; ¹H NMR (CDCl₃, 300 MHz): δ: 4.04 (t, J=6.0 Hz, 2H), 3.27 (t, J=6.2 Hz, 2H), 2.00 (s, 3H), 1.76-1.52 (m, 4H).
¹³C NMR (75 MHz, CDCl₃) δ: 170.82, 63.55, 50.84, 25.73, 25.39, 20.73. 81% yield, clear oil.

References:

Indiana University Research and Technology Corporation;Carlson, Erin;Trader, Darci;Sidebottom, Ashley US2015/240006, 2015, A1