N-Butyl azide

To a flask containing 34.5 gm (0.53 mole) of sodium azide in 70 ml of water and 25 ml of methanol is added 68.5 gm (0.50 mole) of n-butyl bromide while stirring at room temperature. The resulting mixture is heated and stirred on a steam bath for 24 hr. The bottom layer of n-butyl bromide disappears after this time and a top layer of crude n-butyl azide forms. The crude azide is separated and then treated overnight with alcoholic silver nitrate to remove traces of butyl chloride. The mixture is then filtered, washed with water, and distilled behind a safety barricade to yield 40.0 gm (90 %) of n-butyl azide, b.p. 106.5°C (760 mm), n 9 5 1.4152, d29-5 0.8649. (NOTE n-Butyl azide and methanol form an azeotrope (b.p. 60°C) from which the azide is liberated by the addition of a saturated solution of calcium chloride.)... 

The photoreactions of higher alkyl azides were studied by Barton and CO-workers in connexion with the synthesis of the alkaloid conessine . They reported that inadiadon of n-butyl azide (4) in ethanol or ether produced pyrrolidine (5) in yields of 22% cuid 14% respecdvely, together with the imine (6). -Heptyl azide was reported... 

Alkydichloroboranes3 can be used equally well. Thus the reaction of cyclohexyldi-chloroborane with n-butyl azide gives N-n-butylcyclohexylamine in 95% yield. 

Ketones n-Butyl azide. Periodates. Potassium r-butoxide. 

Alkyl isocyanates, like n-butyl isocyanate, do not react with different alkyl azides and aryl azides respectively. In contrast, aryl isocyanates 131 react with alkyl azides 130 like n-butyl azide or cyclohexyl azide to yield 1-alkyl-4-aryl-A -tetrazoline-5-ones 132, however, aryl isocyanates do not react with aryl azides. The reactions take place within some hours and up to several days at elevated temperatures, ranging from 55 to 130 °C, and are performed in benzene or without solvent (Scheme 29A). The addition of aryl azides to acyl isocyanates, such as benzoyl isocyanate or carboalkoxy isocyanates like chloroacetyl isocyanate and trichloroacetyl isocyanate, was unsuccessfully attempted at different reaction conditions [107]. 

Preparation of n-Butyl Azide 32-2. Preparation of Phenyl Azide 32-3. Preparation of Cross-Linked Poly(acrylazide)... 

Neopentyl (2,2-dimethylpropyl) systems are resistant to nucleo diilic substitution reactions. They are primary and do not form caibocation intermediates, but the /-butyl substituent efiTectively hinders back-side attack. The rate of reaction of neopent>i bromide with iodide ion is 470 times slower than that of n-butyl bromide. Usually, tiie ner rentyl system reacts with rearrangement to the /-pentyl system, aldiough use of good nucleophiles in polar aprotic solvents permits direct displacement to occur. Entry 2 shows that such a reaction with azide ion as the nucleophile proceeds with complete inversion of configuration. The primary beiuyl system in entry 3 exhibits high, but not complete, inversiotL This is attributed to racemization of the reactant by ionization and internal return. 

Diamines formed upon photolysis of 6-quinolyl azide in isopropyl-, n-butyl-, and n-hexylamines are very unstable, so they were cyclized to the corresponding 1-substituted imidazo[4,5-/]quinolines by heating the residue obtained after evaporation of the photolysis solvent with formic acid at reflux (82JCS(P 1)421). Instead... 

Butanetriol trinitrate tert-Butoxycarbonyl azide n-Butyl chloroformate... 

N-Butyl-A-2-azidoethylnitramine [84928-98-3] BuN(N02)C2H4N3 See entry energetic compounds See other tv-nitro compounds, organic azides c6h13n5o2... 

All the above reactions of PVC were performed homogeneously in DA-solvents such as HMPA, DMF and dimethylsulfoxide (DMSO). For the practical modification of PVC, the reaction must be conducted under more commercial conditions as in slurry water. As mentioned before, azidation of PVC did not occur in water. However, the reaction proceeded feasibly in water by addition of some cationic surfactant to give, e.g. 8-20% (DS) of azidated PVC at 80°C by use of tetra-n-butyl ammonium chloride (1 ). The use of cationic surfactant was also effective in organic solvents and attracted increased attention as the conception of "phase transfer catalyst" in organic chemistry developed. 

The reaction of sodium azide with N-aryl chloroimines, obtained from benzanilides and thionyl chloride, to form 1,5-disubstituted tetrazoles is catalysed by tetra-n-butyl-ammonium bromide (Scheme 5.26, Table 5.40) [18] in variable yields, but generally <85%. 5-Butyl-2,3-diphenyltetrazolium salts have also been used as catalysts [18, 19]. 1,5-Disubstituted tetrazoles are also obtained from a one-pot sequential reaction of carbodimides with sodium azide and an aroyl chloride in the presence of tetra-n-butylammonium chloride [20]. 5-Chlorotetrazoles are obtained from the catalysed reaction of aryldichloroisocyanides with sodium azide (Scheme 5.26) [21],... 

Cu(N3)a], mw 379.92, N 51.62%. Two isomers are known n-Butyl salt, expl at 178 80° and iso-Butyl salt, mp 125° expl at 203° both compds expl also under impact. These and other complex salts of cupric azide,... 

Unsymmetrically substituted tetra- and penta-n-butyl borazines are obtained by thermal decomposition of dibutylazidoborane 100> with the elimination of butene. Because of the hazards of handling boron azides, this method cannot be recommended. 

C4H9NO butan amide 541-35-5 489.15 42 843 1.2 3864 C4H10N4O2S n-butyl amido sulfuryl azide 13449-22-4 450.15 39.116 1,2... 

All of the azides investigated were time-dependent inhibitors at millimolar concentrations and the inhibition was reversible in each case, with hepatic glutathione 5-transferase proving the most sensitive enzyme. Inhibitor potency appears to depend upon the substrate employed, -heptyl and allyl azides (60) and (62) being the most potent with NBC, and -butyl and -hexyl azide (57) and (59) when DNCB was included in the assay. Kinetic studies, where the GSH and DNCB concentrations were independently varied, indicated that compounds (61),(63) and (64) were noncompetitive inhibitors, while allyl azide (62) and the n-alkyl azides (56)-(60) inhibited the enzyme in a competitive manner. From these observations, the authors speculate that, in a process reminiscent of that known to occur with alkyl and aryl halides, glutathione 5-transferase may catalyse the conjugation of azides with GSH in vivo. 

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