Formamide azide

Iodine Acetaldehyde, acetylene, aluminum, ammonia (aqueous or anhydrous), antimony, bromine pentafluoride, carbides, cesium oxide, chlorine, ethanol, fluorine, formamide, lithium, magnesium, phosphorus, pyridine, silver azide, sulfur trioxide... 

The reaction of the -C(Hal)=N-function with azide ion or hydrazoic acid is known to give the tetrazole system. As part of a mechanistic study of the one-pot synthesis of an azadibenzoporphyrine in 84% isolated yield from reaction of a 1-bromobenzopyrromethene hydrobromide 74 with sodium azide at 140 °C, 74 was treated with azide at lower temperature (60 °C) in an attempt to isolate the proposed azide mechanistic intermediate 75 however, the fused tetrazole 76 was isolated in 47% yield (identified by X-ray analysis) (Equation 4) <1999MI530>. Upon heating a dimethyl formamide (DMF) solution of tetrazole 76 to 140°C for 1 h, the desired porphyrin was indeed obtained in 14% yield, consistent with the temperature-dependent equilibrium between tetrazole and azide that has been observed with some fused tetrazoles. 

Der genauc Mechanismus dieser Reaktion ist nicht bekannt. Die Azide werden durch Reaktion der ent-sprechenden Jodide mil iiberschiissigem Lithium-azid in Dimethyl-formamid (4 mljg Lithiumazid 75° 16 h) hergestellt. 

It has been found32 that treatment of methyl 4,6-dichloro-4,6-dideoxy-a-D-gaIac-topyranoside 2,3-di(chlorosulfate) (8) with sodium bromide in N,N-dimethyl-formamide at room temperature affords methyl 4,6-dichloro-4,6-dideoxy-o -D-galactopyranoside and its 2- and 3-mono(chlorosulfate) derivatives. These three products were also formed, in addition to a mono(azidosulfate) derivative, when 8 was treated with sodium azide in N,N-dimethylformamide at room temperature. 

Azidoformamide. See Carbamyl Azide under Formamide and Beil 3, 129 (59)... 

Sulfuryl Azide Chloride. N3S02.01 mw 141.54 N 29.74% colorl liq bp 116-17° d 1.44g/cc. Sol in benz, chlf and methylene chloride. Prepn is by reacting Na azide and sulfuryl chloride in dimethyl formamide soln at 25° for 18 hrs with stirring. The prod of this reaction is then vac distld off at 25° and collected in a —45° liq N2 cooled trap. A 90% yield is reported. Sulfuryl azide chloride has a mech shock sensy si less than NG. Rapid heating may cause an expin. 

D-xylitol (59,81%), and 2- O -acetyl-1,4-anhydro-6-deoxy-3,5- 0-( 1,1,3,3-tetraiso-propyldisiloxan-l,3-diyl)-D-allitol (60,77%). The reported yields appeared to be independent of the anomeric configuration of the substrates, prepared in two steps from the corresponding glycofuranosyl azides, via the formamides. 

The submitters originally used methanesulfonyl azide,4 but the Board of Editors of Organic Syntheses requested substitution of the much less shock sensitive reagent 4-dodecylbenzenesulfonyl azide. The use of methanesulfonyl azide has previously been recommended,43 since excess reagent as well as certain formamide by-products can be easily separated from the desired diazo ketone product during workup by extraction into dilute aqueous base. 

Two German patents by Muller describe preparative methods which avoid the use of hydrazoic acid by heating sodium azide with ammonium chloride or sulfate in aqueous solution. A recent Japanese patent describes a reaction between sodium azide and ammonium carbamate in liquid ammonia to give ammonium azide. Evans, Yoffe, and Gray have suggested the reaction of sodium azide with ammonium chloride in iV,iV-dimethylformamide. A modification of the last method has been made it involves the reaction of sodium azide and ammonium sulfate in dimethyl-formamide to give anhydrous ammonium azide of high purity. 

Reaction of poly(vinyl chloride) with sodium azide in dimethyl-formamide incorporates azide groups to yield a photocross IinkabIe... 

Carboxamides of the tricyclic compounds 244 (n = 1, R = CONH2) and 389 (w = 1, R = CONH2) were obtained from the appropriate esters or from carboxylic acids with ammonia, via mixed anhydrides. N-Substi-tuted carboxamides of the pyrido[l,2-fl]quinazolinones 211 (R = CONHR ) were prepared directly from the corresponding acids with amines in the presence of diphenylphosphoryl azide and triethylamine in dimethyl-formamide at — S C " or were obtained from esters with amines. ... 

V-Dimethylchlorosulfitomethaniminium chloride (54), prepared from thionyl chloride and dimethyl-formamide, together with sodium azide is useful for the direct preparation of acyl azides from carboxylic acids (equation 35). ... 

Toluenesulfonic anhydride, 1177 p-Toluenesulfonylanthranilic acid, 1181 p-ToIuene ulfonyl azide, 1178-1179 Toluenesulfonyl chloride, 235, 295, 371, 441, 662, 1088-1089, 1179-1184, 1280 / Toluenesulfonyl chloride-Diniethyl-formamide, 1184-1185... 

In a related reaction involving a sugar, Guthrie and Murphy noted that the azido derivative (254) gives, with sodium azide in iV,Af-dimethyl-formamide, the Sn2 product (265), and that the analogous compound. 

Hybridization buffer components Formamide (molecular biology grade), 20x SSC (0.3M sodium citrate, 3.0M sodium chloride, 0.1% (w/v) sodium azide), 10% (w/v) Ficoll Type 400 prepared in water, and 2M sucrose containing 0.1% (w/v) sodium azide. 50mL of each component is sufficient for initial optimizations. 

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