Sodium azide, reaction with -butyl

Sodium azide, reaction with l butyl chloroacetate, 46, 47 reaction with diazomum salt from o amino-f> -ni trobiphcny L, 46, 86 Sodium chlorodifluoroacetate, 47, SO reaction with tnphenylphosphme and benzaldehyde, 47, SO Sodium ethoxide, 46, 2S reaction with diethyl succinate, 46,2S Sodium formate as reducing agent in preparation of palladium catalyst, 46, 90... 

Sodium azide, reaction with 1-butyl chloroacetate, 46, 47 reaction with diazonium salt from -ammo-/> -nitrobiphcnyl, 46,... 

Silver fluoborate, reaction with ethyl bromide in ether, 46, 114 Silver nitrate, complexing with phenyl-acetylene, 46, 40 Silver oxide, 46, 83 Silver thiocyanate, 46, 71 Sodium azide, reaction with f-butyl chloroacetate, 46, 47 reaction with diazonium salt from fi-amino-/> -nitrobiphenyl, 46,... 

N-Bromosucdnimide in bromination of o-nitrotoluene to form < -nitro-benzyl bromide, 4G, 81 Butadiene, 46, 106 BuTADrVNE, DIPHENYL, 46, 39 A - -Bhtenolide, 46, 22 (-Butyl alcohol in synthesis of phenyl (-butyl ether, 46, 89 (-Butyl azidoacetate, 46, 47 hydrogenation of, 46, 47 (-Butyl chloroacetate, reaction with sodium azide, 45, 47 (-Butyl hypochlorite, reaction with cy-clohexylamine, 46,17 (-Butylthiourea, 46, 72 (-Butylurea, 46, 72... 

Azide 367 is prepared from 4-r -butyl-2-nitroaniline in 76% yield by its diazotization followed by treatment with sodium azide. In a 1,3-dipolar cycloaddition with cyanoacetamide, azide 367 is converted to triazole 368 that without separation is directly subjected to Dimroth rearrangement to give derivative 369 in 46% yield. Reduction of the nitro group provides ortfc-phenylenediamine 371 in 91% yield <2000EJM715>. Cyclocondensation of diamine 371 with phosgene furnishes benzimidazol-2-one 370 in 39% yield, whereas its reaction with sodium nitrite in 18% HC1 leads to benzotriazole derivative 372, which is isolated in 66% yield (Scheme 59). Products 370 and 372 exhibit potassium channel activating ability <2001FA841>. 

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],... 

The first synthesis of the parent compound of the benzo[4,5]thieno[2,3-f]pyrrole ring system 387 <2003T1477> and its derivatives was accomplished using the same synthetic sequence (Scheme 42). Starting with 2-methyl-benzo[ ]thiophene-3-carbaldehyde 388, an intermediate 389 was obtained. Treatment of bromo compound 389 with sodium azide in ethanol led to the stable triazoline 390. 1,3-Dipolar cycloreversion of 390 was induced by a catalytic amount of />-TsOH to give the parent 2//-benzo[4,5]thieno[2,3-c]pyrrole 387. Alternatively, direct treatment of bromo compound 389 with excess ammonia furnished 387 in one step. Compound 387 was treated with di-/-butyl dicarbonate and 4-dimethylaminopyridine (DMAP) to give iV-BOC derivative 391. Reaction of 389 with... 

The synthesis of the amino alcohol (5S,6S)-6-amino-5-decanol begins with reaction of the 1-chloropentylboronic ester (Section 1.1.2.1.3.1.) with sodium azide under phase-transfer conditions to form the a-azido boronic ester, which yields the a-chloro- -azidoalkyl boronic ester (1) [yield 92 % 95 % de] with (dichloromethyl)lithium under the usual conditions. The reaction of 1 with butylmagnesium chloride is unusual in that it requires zinc chloride in order to accomplish the replacement of chlorine by butyl to form /J-azidoalkyl boronic ester 2 without boron-azide /1-elimination. Standard peroxidic deboronation and reduction of the azide complete the synthesis15. 

Preparation of 1 -butyl-3-p-tolylsulfonylurea by the reaction of butyl-carbamoyl azide with sodium p-toluene sulfinate [104]. 

Goodman and Chorev 75 found that the required a-aminoacyl azides 14 are best prepared by reaction of the mixed anhydride of the amino acid with sodium azide. This method led to slightly better yields than the nitrosylation of TV-formylaminoacyl hydrazide. Curtius rearrangement of the a-aminoacyl azide 14 yielded the isocyanate 16, which was subsequently trapped as 17 or 18 as shown in Scheme 2. Comparable yields were obtained by nitrosylation with tert-butyl nitrite. 76 Other methods of acyl azide formation have rarely been employed for PMRI-peptide synthesis. Only Fincham et al. 11 reported the use of trimethylsilyl azide to synthesize an acyl azide en route to a PMRI-peptide. 

Under the appropriate conditions it undergoes hazardous reactions with Al, tert-butyl azido formate, 2,4-hexadiyn-l,6-diol, isopropyl alcohol, K, Na, sodium azide, hexafluoroisopropylideneamino lithium, lithium. When heated to decomposition or on contact with water or steam it will react to produce toxic and corrosive fumes of CO and Cr. Caution-. Arrangements should be made for monitoring its use. 

This azide, prepared by adding a solution of n-butyl bromide to a slurry of of sodium azide in water, cleaves ketones of the type ArCOCHjR in benzene or nitrobenzene at 70-90° in the presence of a catalytic amount of sulfuric acid to two carbonyl components. Acetophenone gives benzaldehyde (80%) and formaldehyde (83%) propiophenone gives benzaldehyde and acetaldehyde. The reaction is interpreted as involving combination of the azide with the coiyugate acid of the ketone, release of nitrogen from the diazonium cation with elimination of water, hydration, and cleavage. 

In a new simplified preparation,1 the reagent is obtained directly and in high yield by the reaction of p-methoxybenzyl chloroformate with sodium azide in the presence of pyridine (compare preparation of /-butyl azidoformate, 2,48). 

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