4-Methylbenzenesulfonamide

The marked tendency of l-oxa-2-azaspiro[2.5]octane (52) to transfer its NH group gives rise to smooth reactions with sulfur compounds. Aminothiocyanate (94) is formed in 91% yield at room temperature within one minute and 4-methylbenzenesulfonamide (95) is formed within five minutes in 84% yield from the sulfinate (68TH50800). 

Chemical Name (1S-(endo,endo)] -N-( [(3-hydroxy-4,7,7-trimethylbicyclo[2.2.1 ] hept-2-yl)-amino] carbonyl] -4-methylbenzenesulfonamide... 

Chemical Name N-[(butylamino)carbonyl] -4-methylbenzenesulfonamide Common Name 1-butyl-3-(p-tolylsulfonyl)urea Structural Formula ... 

CN (+)-5-[l-hydroxy-2-[[2-(2-methoxyphenoxy)ethyl]arnino]ethyl]-2-methylbenzenesulfonamide monohydrochloride... 

RN 565-33-3 MF C HjiNjCjS MW 311.41 EINECS 209-276-9 CN 3-amino-A-[(cyclohexylamino)carbonyl]-4-methylbenzenesulfonamide... 

C1DH9IJN2O3 727-56-0) see lodamide 3-acetylainino-4-methylbenzenesulfonamide (CjH,2N203S 17485-44-8) see Metahexamide... 

Dipping solution Dissolve 10 g trichloroacetic acid and 0.4 g chloramine T (N-chloro-4-methylbenzenesulfonamide sodium salt) in a mixture of 80 ml chloroform, 18 ml methanol and 2 ml water [11]. 

For the preparation of N- 2-(methoxyphenyl)cthyl ]-4-mcthylbcn-zenesulfonamide (1) from Ameba resins A and Ba-Bd, 100 mg (0.089 mmol) Ameba resin A was added to a glass peptide reaction vessel, suspended in 3.0 mL 1,2-dichloroethane (DCE note 2), and treated with 26 pL (0.18 mmol, 2.0 Eq.) 2-(4-methoxy-phenyl)ethylamine (note 2) and 38 mg (0.178 mmol, 2.0 Eq.) sodium triacetoxyborohydride (note 2). The suspension was shaken for 1 h treated with 5 mL MeOH filtered on a glass frit and washed with DCM (2x5 mL), DMF (2x5 mL), MeOH (2 x 5 mL), and DCM (2x5 mL). The resin was dried under vacuum (0.5 torr) at room temperature overnight. The resin was suspended in 1.5 mL DCM, treated with 155 pL (0.89 mmol, 10.0 Eq.) N,N-diisopropylethylamine (note 2) and 85 mg (0.445 mmol, 5.0 Eq.) p-toluenesulfonyl chloride (note 2), and shaken for 3.5 h. The reaction mixture was filtered on a glass frit, washed with DCM (2 x 5 mL), DMF (2x5 mL), MeOH (2x5 mL), and DCM (2 x 5 mL), and dried under vacuum (0.5 torr) at room temperature for 2h. The resin was treated with 2.5 mL of a solution of 5% trifluoroacetic acid (note 2) in DCM, shaken for 15 min, filtered on a glass frit, and washed with DCM (3x5 mL). The combined filtrate and washings were concentrated and dried under vacuum (0.5 torr) at room temperature overnight to afford 18.0 mg (66%) N- [2-(methoxyphenyl)ethyl] -4-methylbenzenesulfonamide (1). 

The aza-MBH model reaction of N-benzylidene-4-methylbenzenesulfonamide and methyl vinyl ketone in the presence of catalyst 166 (10mol%) furnished different yields and revalues ofthe resulting adduct (S)-l (Scheme 6.159), when using long-stored (adduct 1 78% yield 70% ee) or freshly prepared (adduct 1 12% yield 16% ee) sulfonamide starting material under otherwise identical conditions. H... 

In contrast, when a twofold excess of the dialkoxydihydropyrazine is used, then 2 1 adducts are obtained. This has been demonstrated18 by reacting A,7V-bis(2-iodoethyl)-4-methylben-zenesulfonamide with two equivalents of the lithiated D-valine/alanine-based dialkoxydihydropyrazine 8 to give 7V.fV-bis 2-[(2S,57 )-2,5-dihydro-5-isopropyl-3,6-dimethoxy-2-mcthyl-2-pyrazinyl]ethyl -4-methylbenzenesulfonamide (9) in high yield and >95% de. The adduct can be hydrolyzed in high yield to the corresponding amino acid methyl ester 10. 

Widenhoefer and co-workers have developed an effective protocol for the asymmetric cyclization/hydrosilylation of functionalized 1,6-enynes catalyzed by enantiomerically enriched cationic rhodium bis(phosphine) complexes. For example, treatment of dimethyl allyl(2-butynyl)malonate with triethylsilane (5 equiv.) and a catalytic 1 1 mixture of [Rh(GOD)2] SbF6 and (i )-BIPHEMP (5 mol%) at 70 °G for 90 min gave the silylated alkylidene cyclopentane 12 in 81% yield with 98% de and 92% ee (Table 4, entry 1). A number of tertiary silanes were effective for the rhodium-catalyzed asymmetric cyclization/hydrosilylation of dimethyl allyl(2-butynyl)malonate with yields ranging from 71% to 81% and with 77-92% ee (Table 4, entries 1-5). Although the scope of the protocol was limited, a small number of functionalized 1,6-enynes including A-allyl-A-(2-butynyl)-4-methylbenzenesulfonamide underwent reaction in moderate yield with >80% ee (Table 4, entries 6-8). 

Tolbutamide Sodium USP. Orinase Diagnostic [473-41-6] (A- [(butylamine)carbonyl]-4-methylbenzenesulfonamide, mono sodium salt), mol wt 292.33, is a white to off-white practically odorless crystalline powder having a slighdy bitter taste. It is freely soluble in water, soluble in alcohol and chloroform, and very slightly soluble in ether and can be prepared by dissolving tolbutamide in aqueous NaOH. 

A mixture of N-benzyl-2-(2-methoxyphenoxy)ethylamine, methyl ethyl ketone, and 5-bromoacetyl-2-methylbenzenesulfonamide was refluxed with stirring. After cooling the reaction mixture, ethyl ketone was distilled off under reduced pressure and the residue formed was dissolved in benzene. Then, ether was added to the solution and after removing the hydrobromide of N-benzyl-2-(2-methoxyphenoxy)ethylamine precipitated, the solvent was distilled off under reduced pressure to provide a viscous oily product. 

In 200 ml of methanol was dissolved 20.0 g of 5- l-hydroxy-2-[N-benzyl-2-(2-methoxyphenoxy)ethylamino]ethyl -2-methyl-benzenesulfonamide. After adding thereto 20 ml of ethanol containing about 10% hydrogen chloride and 1.0 g of 10% palladium charcoal, the mixture was shaken in hydrogen gas stream. When the absorption of hydrogen stopped, the catalyst was filtered away and the filtrate was distilled off under reduced pressure. The residue was dissolved in 100 ml of ethanol while it was hot and the solution was allowed to stand overnight in ice chamber, whereby 12.8 g of the a-type crystals of 5- 1-hydroxy-2-[2-(2-methoxyphenoxy)ethylamino]ethyl>-2-methylbenzenesulfonamide were obtained as the colorless crystals, melting point 169°-171°C. 

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