Pentyl azide

Pentyl azide. See under Amylazide in Vol 1, A395-R to A396-L... 

Pentafluoronitrosobenzene, 363, 410 Pentyl azide, 271 Peracid oxidation of amines, 323, 363,409 of azo compounds, 355-356 of hydrazones, 362 of hydroxylamines, 364,415 of imines, 406 of oxaziranes, 407 Perchloryl fluoride, 336 Perfluoroalkylureas, 162 Perfluoro-2-azopropene, oxidation of, 432 Periodic acid oxidation, 338 Permonosulfuric acid, see Caro s acid Phenazines, 321... 

In order to illustrate the utility of this method the preparation of pentyl azide is described in Procedure 2-2. 

Pentyl azide 662 A mixture of activated sodium azide663 (27 g), diethylene glycol monoethyl ether ( Carbitol ) (450 ml), and water (75 ml) is placed in a 1-1 three-necked flask fitted with a reflux condenser, thermometer, and stirrer the mixture is stirred while pure pentyl iodide (60 g) is added in one portion. The solid dissolves within a few minutes. Whilst being continuously stirred, the mixture is heated during 3 h to 95° and then kept at that temperature for 20 h. It is then cooled and poured in two portions into separate portions of ice-water (each 800 ml). The aqueous phases are separated and extracted twice with ether (200-ml batches). The ether solutions are united with the previous organic phases, and the ether is evaporated. The residue (42 g) is fractionated in a vacuum, giving the azide, b.p. 77-78°/112 mm, nD20 1.4266 (27.8 g, 81.4%). 

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