1,3-Disulfonamide

The product separates as a gum from which the supernatant liquid is decanted, and the gum is triturated with 250 cc of water in order to induce crystallization. The crude product thus obtained is recrystallized from 3,200 cc of boiling water and then from 40% aqueous isopropyl alcohol yielding 4,5-dichlorobenzene-1,3-disulfonamide as a white solid, MP 228.5° to 229.0°C. 

The standard synthesis of sydnones (Section 5.03.9.2) has benefited from the use of A,./V,iV, iV -tetrabromobenzene-1,3-disulfonamide (TBBDS) as an efficient promoter of the one-pot conversion of various iV-arylglycines to sydnone products <2006H(68)2343>. Conversion of A-arylglycines to sydnones was achieved in 85 to 95% yield using a combination of NaN02 and AczO in CH2C12 promoted by TBBDS, under mild and neutral conditions. 

The reaction between 4,6-dichlorobenzene-1,3-disulfonamide and CS2 yielded the unusual benzene bis[dithiazine] (105 R = H), which is readily methylated to the derivative (105 R = Me) <84MI 723-01). Displacement of the fluorine atoms and nitro groups from l,3-difluoro-4,6-dinitrobenzene by 1,3-diphenylthiohydrazide (PhCS, NHNHPh) yielded compound (106) <80JOC3677>. 

Cyclothiazide can be prepared by the addition of an excess of ammonia to 5-norbornylenyl-carboxaldehyde. This reaction mixture is then added to a solution of 4-chloro-6-fluorobenzene-1,3-disulfonamide, and the product is precipitated by addition to dilute acid10. Alternate processes similar to the above involve use of the aldehyde-ammonia complex or the aldimine produced in the first step above by variations of the reaction media. 

Cyclothiazide appears to be very stable in the solid state and under ordinary ambient conditions. Cyclothiazide is rapidly decomposed when heated in boiling acidic or basic alcohol solutions and is more rapid in the acidic solution13. By the thin layer chromatography method of Koch13, one of the decomposition products has the same Rf value as 4-amino-6-chlorobenzene-1,3-disulfonamide. 

A mixture of 8.5 g (0.03 mol) of 6-chloro-4-amino-benzene-1,3-disulfonamide, 4.0 g (0.033 mol) of 2,5-endomethylene-A -tetrahydrobenzaldehyde and 25 cc of diethyleneglycol-dimethyl ether was heated for 2 hours at 100°C. During this time the major portion of the initially undissolved crystals went into solution thereafter, the reaction mixture was allowed to stand for 14 hours at room temperature, during which the remaining undissolved crystals also went into solution. The reddish, clear solution thus obtained was admixed... 

Ami no-5-methylben-e-1,3-disulfonamide 2-Amino-5-me(hylben-zene-1,4-disulfonamide... 

F., Walker, R. W., and Wolf, F. J. Gas-Liquid Chromatographic Determination of 4-Amino-6-(trichloroeth-enyl)benzene-1,3-disulfonamide, a New Anthelmintic, in Biological Fluids... 

Ghorbani-Vaghei R, Veisi H (2009) Poly(N, N -dichloro-N-ethylbenzene-1,3-disulfonamide) and A,A,A, A -tetrachlorobenzene-l,3-disulfonamide as novel reagents for the synthesis of A-chloroamines. Nitriles and Aldehydes. Synthesis 6 945-950... 

Ghoibani-Vaghei et al. (2007) reported an efficient rapid and mild methodology for the oxidation of primary and secondary alcohols to the corresponding carbonyl compoimds in presence of N,N,N, N -tetrabromobenzene-l,3-disulfonamide (TBBDA) or poly(N-bromobenzene-1,3-disulfonamide) (PBBS) using microwave irradiation under solvent-free conditions. 

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