DICHLORAMINE T

The Uses of DICHLORAMINE T

Germicide.

The Uses of DICHLORAMINE T

N,N-Dichloro-p-toluenesulfonamide (TsNCl₂) can be used as:????????

• A nitrogen source for the preparation of aziridines from electron-deficient α,β-unsaturated alkenes in the presence of palladium catalyst.??????
• A reagent in the synthesis of dichlorohaloamines by aminohalogenation of functionalized olefins using copper(I) chloride or 4-dimethylaminopyridine (DMAP) catalyst.???????
• A chlorinating agent in the regioselective synthesis of α-mono chlorosulfoxides from dialkyl sulfoxides or alkyl aryl sulfoxides.

Purification Methods

Crystallise it from pet ether (b 60-80o) or CHCl3/pet ether. Dry it in air <55o and store in the dark. It is soluble in CHCl3 (~1:1), *C6H6 (~1:1) and CCl4 (~1:2.5). It is a germicide and antibacterial as it readily liberates chlorine, and it should not smell strongly of chlorine; otherwise it should be purified. Alternatively dissolve ~15g of reagent in 75mL of hot acetic acid and precipitate it by addition of 37mL of N/10 bleaching powder solution (NaOCl), filter off, wash it with a dilute solution of the latter, dry as above (m 78-84o) and recrystallise it. “Sharp drying” will decompose it. [Orton & Bradfield J Chem Soc 993 1927, Krauss & Crede J Am Chem Soc 39 2720 1917, Soper J Chem Soc 1899 1924.] [see also chloramine-T (monochloramine T Na salt) in “Metal-organic Compounds”, Chapter 5]. [Beilstein 11 H I07, 11 I 27, 11 II 63, 11 III 301.]