Nitrobenzenesulfonyl Chloride

Solubility soluble in most common organic solvents. 

Handling, Storage, and Precaution moisture sensitive stable for one year under nitrogen and protected from light at 0 °C. 

Secondary Amine Synthesis from Primary Amines.  

Since the Ns group Is stable under acidic [HCl (10 equiv), MeOH, 60 °C, 4 h] as well as basic [NaOH (10 equiv), MeOH, 60 °C, 4 h] conditions, it can be used for protection of both primary and secondary amines. 

A list of General Abbreviations appears on the front Endpapers 

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R)-Cyanohydrins react with toluenesulfonyl chloride, methanesulfonyl chloride or 4-nitrobenzenesulfonyl chloride without loss of stereochemical purity, and the 2-sulfonyloxy-nitrile reacts with a variety of Sn2 reactions to give a variety of products, such as 2-fluoro nitrile [64], 2-azidonitrile [65] and /V- p h t h a I o yl - p rot e c te d 2-aminonitrile [66], 2-acetoxy nitrile [66], and 2-mercapto nitrile [67]. Hydrogenation of 2-sulfonyloxynitriles with LiAIH4 in good chemical yields and high ee afforded 2-monosubstituted (S)-aziridines [68]. 

Sulfamethizole Sulfamethizole, AfL(5 niethyl-l,3,4-thiadiazole-2-yl)sulfanilamide (33.1.15), is synthesized in two ways. According to the first, 5-amino-2-methyl-l,3,4-thiadiazole is reacted with 4-nitrobenzenesulfonyl chloride to make a nitro derivative (33.1.14), which is then reduced using iron filings in acetic acid to give the desired sulfamethizole. 

S-(+)-3-Chloro-l,2-propanediol Methanesulfonyl chloride Potassium t-butoxide 4-Nitrobenzenesulfonyl chloride Hydrochloric acid Diisopropylethylamine Benzyl chloroformate... 

Tetrahydrofuran (3.2 ml) and S-(+)-3-chloro-l,2-propanediol (0.299 ml, 3.58 mmol, 1.19 eq) are mixed. The mixture of THF (3.2 ml) and S-(+)-3-chloro-1,2-propanediol (0.299 ml, 3.58 mmol, 1.19 eq) is cooled to -16°C and potassium t-butoxide (3.2 ml, 1.0 M) in THF (3.2 mmol, 1.07 eq) is added at less than -10°C. The resulting slurry is stirred at -14-0°C for 1 hour. Then added to the lithium anion mixture while maintaining both mixtures at 0°C, then rinsed in with THF (2 ml). The resultant slurry is stirred at 20-23°C for 2 hour and then cooled to 6°C and a mixture of citric acid monohydrate (0.4459 g, 2.122 mmol, 0.705 eq) in water (10 ml) is added. The resultant liquid phases are separated and the lower aqueous phase is washed with ethyl acetate (12 ml). The organic layers are combined and solvent is removed under reduced pressure until a net weight of 9.73 g remains. Heptane (10 ml) and water (5 ml) are added and solvent is removed 4-nitrobenzenesulfonyl chloride y reduced pressure until a total volume of 5 ml remains. The precipitated product is collected by vacuum filtration and washed with water (7 ml). The solids are dried in a stream of nitrogen to give (R)-[N-3-(3-fluoro-4-(4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methanol. 

To a slurry of (R)-[N-3-(3-fluoro-4-(4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methanol (43.0 g, 145 mmol) and triethylamine (36 g, 355 mmol) in methylene chloride (450 ml) at 0°C is added a mixture of 4-nitrobenzenesulfonyl chloride (32 g, 145 mmol) in methylene chloride (55 ml). The mixture is stirred in a 0°C bath for 30 min and then quenched with hydrochloric extracted again with methylene chloride (200 ml). The combined organic extracts are then concentrated column chromatographed (silica gel, methanol/methylene chloride 1-2/98-99, about 8 L). The appropriate fractions are combined and concentrated to give the (R)-[N-3-(3-fluoro-4-(4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methanol 4-nitrobenzenesulfonate ester. 

L-Histidine (2) was converted to (S)-2-hydroxy-3-(imidazol-5-yl)pro-pionic acid (38), with retention of configuration using silver nitrite and orthophosphoric acid. The acid (38) was esterified and the ester (39) treated with 4-nitrobenzenesulfonyl chloride. With the latter treatment, the hydroxyl group was esterified and the N1 atom was sulfonated. Walden inversion of the reaction product (40), using lithium bromide in 2-butan-... 

Oxidation of alkyl 4-nitrobenzenesulfonates. The oxidation of primary alcohols to aldehydes by dimethyl sulfoxide requires temperatures around 100° or introduction of acids or heavy metal ions. In a new procedure the alcohol is converted into the 4-nitrobcnzenesulfonate ester by reaction with 4-nitrobenzenesulfonyl chloride and... 

Nosyloxyesters undergo substitution reactions with inversion of configuration (Scheme 15). The corresponding nosyl lactate 98 is prepared in quantitative yield from 97 upon treatment with 4-nitrobenzenesulfonyl chloride in the presence of triethylamine and DMAP [34]. Reaction of 98 with sodium azide in DMSO (55 °C) gives the (R)-azidoester 99. Hydrolysis of the ester with lithium hydroxide in aqueous THF furnishes the azido acid 101 (92% ee). Reduction of the azide group is easily accomplished either under catalytic conditions or with triphenylphosphine and water. 

Related Reagents. ferf-Butylsulflnyl Chloride Di-teri-butyl Disulfide Benzenesulfonyl Chloride Methanesulfonyl Chloride 2-Nitrobenzenesulfonyl Chloride 4-Nitrobenzenesulfonyl Chloride 2,4-Dinitrobenzenesulfonyl Chloride. ... 

Related Reagents. 4-Nitrobenzenesulfonyl Chloride 2,4-Dl-nitrobenzenesulfonyl Chloride 2-Nltrobenzenesulfonamide. 

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