1H-Tetrazole

Chemical Name Sodium 7-(D-2-formyloxy-2-phenylacetamldo)-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate... 

To 13 of ethyl acetate were added 85.1 g (2.59 mols) of 7-emino-3-(1 -methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid and 1,361 g (10.37 mols) of monotrimethylsilyl acetamide, and the mixture was stirred at 50°C until a clear solution was obtained. The solution was cooled to 20°C and 514 g (2.59 mols) of 0-formyl mandeloyl chloride was added at a rate such that the temperature of the reaction solution was maintained between about 20°C to 25°C with ice-cooling. 

The reaction mixture was stirred for 1.5 hours at about room temperature after the addition of the mandeloyl chloride was completed. Five liters of water were then added to the reaction mixture and the diluted mixture was stirred for about 10 minutes. The organic layer was separated and was washed twice with water. The combined washes are extracted with 1.5 of ethyl acetate and the extract is combined with the washed organic layer, The whole was dried over magnesium sulfate, filtered and evaporated in vacuo on a 25°C water bath to yield 1,460 g of product,7-(D-2-formyloxy-2-phenylacetamido)-3-(1-methyl-1H-tetrazol-5-ylthlomethyl)-3-cephem-4-carboxyllc acid, as a yellow foam. 

Synthesis of ( )-trans-6-[4,4-bis(4-fluorophenyl)-3-(1 -methyl- 1H-tetrazol-5-yl)-1 (E), 3-[2- uC]butadienyl-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one... 

Although addition of activated phosphoramidite to hemiacetals of manno-pyranoses under thermodynamic control has been reported to deliver exclusively a-phosphates in some cases,43 anomeric mixtures with preponderance of a-anomer have been reported in other examples.10,44 Since formation of phosphorotetrazolidite is a rate-limiting step of the process, initial activation of phosphoramidite followed by addition of nucleophilic hemiacetal should accelerate condensation and favour the formation of the thermodynamic a-product. Indeed, reaction of hemiacetal 101 with dibenzyl phosphorotetrazolidite assured exclusive a-selectivity of the resulting glycosyl phosphate 102.43 The accumulation in the reaction mixture of mildly acidic 1H-tetrazole, which is liberated upon reaction of tetrazolidite with hydroxylic component, could also favour predominant formation of the a-phosphate (Scheme 18, A). Conventional hydrogenolysis afforded the a-mannosyl phosphate 103. 

H-tetrazole (2 equiv), Pr2NP(OBn)2 (1 equiv) then m-CPBA... 

Given the role that low thresholds of 5-AT and 1H tetrazole impurities clearly play in the successful synthesis of DBX-1 from NaNT, we endeavoured to develop a procedure for synthesizing pure NaNT as efficiently as possible, while avoiding the tedious, time consuming, and reduced yield Cu11 titration and filtration, which is currently required. As an added refinement, we also desired to eliminate the handling of the intermediate acid salt of copper(II) 5-nitrotetrazolate, Cu(NT)2 HNT ... 

Hydrazo-bis-1H-Tetrazole. See Bis (5-Tetra-zole)-hydrazine in Vol 2 of Encycl, p B157-R and the following addnl refs Refs 1) F.R. Benson, ChemRevs 41, 8 (1947)... 

A recent study of the structural analysis by single cryst methods (Refs 14 15) shows that Tetracene is the zwitterion (guanidinium) of 1-Ami no-1-[(1H-tetrazole-5-yI)azo]- guanidine Hydrate of structure ... 

Aminotolyltetrazoles and derivs 1 A265—A267 1,1 -azo-5,5 -di(p-tolyl) tetrazole 1A266—A267 l,l-(N-dichloramino)-5-(p-tolyl)-a(or 1H)-tetrazole 1 A266... 

The experimental heat of formation of tetrazole of 28.11 eV, compared to values for pyrazole (39.391 eV), imidazole (39.790 eV) and 1,2,4-triazole (34.377 eV), suggests that tetrazole is less stable than the lower azoles (66JCP759). Dewar has calculated resonance energies of 26.0 kcal mol-1 for 1H-tetrazole and 29.25 kcal mol 1 for 27/-tetrazole which compare with values for pyrazole (35.5), imidazole (22.9) and Iff-1,2,3-triazole (27.9 kcal mol-1) (66JCP759). 

The intramolecularity of the thermal rearrangement of 1 -aryl-5-allyloxy-1H-tetrazoles to l-aryl-4-allyl-l,4-dihydrotetrazol-5-ones has been investigated through... 

Acetonehydrazone-a(1H)- tetrazole, called Acetone 5-tetrazolylhydrazone by Benson, (Tetrazolon-iso-propyliden- hydrazon, in Ger), (CHS) C N NH-C-NH-N, raw 140.15,... 

Amino-l-(m-nitrophenyl)-a-tetrozole, 5-Amino-l-(3 -nitrophenyl)-1H-tetrazole or l-(m-Nitro-phenyl)-5-aminotetrazole, H2N>C-N(C6H4-N02 )-N. 

Tetrazolyl)-4//-pyrido[l,2-u]pyrimidin-4-one 159 (R = H) was prepared in 65% yield in a one-pot reaction when 2-aminopyridine, ethyl 1H-tetrazol-5-ylacetate, triethyl orthoformate, and aluminum chloride were heated in 1,1,2,2-tetrachloroethane under nitrogen at 120°C for 3 days (84USP4474953). 

OXA-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(2-CARBOXY-2-(p-HYDROXYPHENYL)ACETAMIDO)-7-METHOXY-3-(((1-METHYL-1H-TETRAZOL-5-... 

Table 27 Reaction of 2-propyl-5,6,7,8-tetrahydro-3/-/-cycloheptimidazol-4-one with 5-(4-bromomethyl-biphenyl-2-yl)-1-fert-butyl-1H-tetrazole 327 (Equation 58) <2006CPB706>...

Triorganotin derivatives of 1 -phenyl- 17/-tetrazole-5-thiol also tend to self-assemble in the solid state359-361. For example, tribenzyltin 1 -phenyl-1H-tetrazole-5-thiolate, Bz3SnSCN4Ph (161), forms a linear coordination polymer with intermolecular Sn—N distances of 2.559(12) and 2.676(10) A and intramolecular Sn—S distances of 2.565(4) A359, whereas trimethyltin 1-phenyl-177-tetrazole-5-thiolate, Me3SnSCN4Ph360, self-assembles to give trimers. 

Acetophenonehydrozone—a(1H)—tetrazole or 5—[(Methylphenylmethylene)-hydrnzine]-a(1H)—tetrazole, called in Ger Tetrazolon— a—phenMthylidenhydrazon or 5—a—Phenathyli-denhydrazinotetrazol,... 

D.B.Murphy S.Helf,JACS 76,1433(1954) S-Amino-l-phenyl-o-fetrasole, 5-Amino-1-phenyl-1H-tetrazole or l-Phenyl-5-omino-tetrazole [Called in Beil 1-Phenyl-tetrazoloo-... 

Nitrosamino-1-phenyl-a tetrozole or 5 Nitrosamino-1-phenyl>1H>tetrazole [Called in Beil 1-Phenyl-tetrazol-diazonium-hydroxyd-... 

AMlNO-a-TETRAZOLE or 5-AMIN0<1H-TETRAZOLE (One of the Ger names is Tetrazolon-imid and Thiele called it "Amidotetrazotsaure ). It is usually designated as 5-ATZ, or... 

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