11-Azido-1-undecanethiol synthesis
- Product Name:11-Azido-1-undecanethiol
- CAS Number:668420-70-0
- Molecular formula:C11H23N3S
- Molecular Weight:229.3854
668420-75-5
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Yield:668420-70-0 63%
Reaction Conditions:
with acetyl chloride in methanol at 0; for 24 h;Inert atmosphere;
Steps:
2 Synthesis of 11-azido-1-undecanethiol (1)
Under argon at 0 °C 7 mL (95 mmol) acetyl chloride were added to 40 mL methanol. The solution was stirred for 30 min and then 1.14 g (4.2 mmol) 11-azido-1-undecanol,1-thioacetate 9 in 10 mL methanol was added. Stirring was continued for 24 h. 300 mL of a saturated sodium bicarbonate solution was added. The mixture was extracted three times with 100 mL of diethyl ether and then washed with a sodium bicarbonate solution and water. The ether phase was washed with a sodium bicarbonate solution and water. The organic layer was separated and dried by filtration over cotton wool. The residue was dried again in vacuum and then purified by column chromatography (silica gel, CH2Cl2). The dark brown residue was distilled in vacuum to give an orange-yellow liquid. Yield: 608 mg (2.65 mmol, 63%). TLC (CH2Cl2): 0.74. 1H NMR (200 MHz, CDCl3): δ=3.24 (t, 3J=6.9 Hz, 2H, CH2N3), 2.56-2.45 (m, 2H, CH2SH), 1.67-1.52 (m, 4H), 1.41-1.26 (m, 14H). 13C NMR (200 MHz, CDCl3): δ=51.6 (CH2N3), 34.2, 29.6, 29.3, 29.2, 29.0, 28.5, 26.9, 24.8. IR (NaCl, Film): ν=2927, 2854 (s, CH), 2095 (s, N3), 1465 (m), 1349 (w), 1260 (m), 722 (w). MS (EI, 70 eV): m/z: 229 [M].
References:
Wichmann, Andre;Schnurpfeil, Günter;Backenk?hler, Jana;Kolke, Lena;Azov, Vladimir A.;W?hrle, Dieter;B?umer, Marcus;Wittstock, Arne [Tetrahedron,2014,# 36,p. 6127 - 6133]
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