2-Chloro-5-nitrobenzenesulfonyl chloride

Solid

Preparation of 1 -(2-(2, 5-dichlorophenoxy)-5-nitrophenylsulfonyl)piperazine 40; [00255] Compound 40 was synthesized as shown in Scheme 5. Scheme 5 [00256] 2-Chloro-5-nitrobenzene-l-sulfonyl chloride 37.; To an ice-bath chilled solution of cone. HCl (100 mL) was added 2-chloro-5-nitroaniline (10 g) portion-wise. When complete dissolution was achieved, an aqueous solution of sodium nitrite (6.0 g in 50 mL water) was added dropwise and the resulting reaction mixture was stirred at 0 [00300] 2-Chloro-5-nitrobenzene-l-sulfonyl chloride 37. To an ice-bath chilled solution of cone. HCl (100 mL) was added 2-chloro-5-nitroaniline (10 g) portion-wise. When complete dissolution was achieved, an aqueous solution of sodium nitrite (6.0 g in 50 mL water) was added dropwise and the resulting reaction mixture was stirred at 0 General Procedure VII-BEPOClTo chlorosulphonic acid (14.96 g, 8.45 mL) was added sodium 2-chloro-5-nitrobenzenesulfonate (5.56 g, 21.4 mmol) with stirring at 5-10 °C. The reaction mixture was stirred at 130 °C for 4 h and then poured onto 120 g of ice with vigorous stirring. After stirring for 10 min, the gray precipitate was filtered and pressed dry. The solid was dried overnight in a desiccator under vacuum (4.43 g, 81percent yield, m.p. 88-90 °C).General procedure: Chlorosulfonylation of 4-nitro-1-halobenzene (16a and16b). A solution of 4-nitro-1-halobenzene (15a and 15b) in chlorosulfonic acid was slowly heated to 120 2-Chloro-5-nitrobenzene-l-sulfonyl chloride (SG3-128): SG3-128 was prepared using the method previously reported by Goldfarb and Berk. (New Compounds. Derivatives of 2, 5- Diaminobenzenesulfonamide. J. am. Chem. Soc. 1943, 65, 738-739). A mixture of 4- chloronitrobenzene (3.94 g, 25 mmol) and chlorosulfonic acid (8.31 mL, 125 mmol) was stirred and heated overnight at 120 °C. The solution was cooled and poured into crushed iced in an ice bath and the precipitate filtered. Recrystallization of the resulting solid from carbon tetrachloride (CAUTION) provided the title compound as a light brown solid (0.342 g, 14percent). Mp: 87-88 °C (lit. Mp 85-87 °C). NMR (400 MHz, CDCb) δ: 9.01 (d, J= 2.6 Hz, 1H), 8.51 (dd, J= 8.7, 2.6 Hz, 1H), 7.88 (d, J= 8.7 Hz, 1H).SG3-128 was prepared using the method previously reported by Goldfarb and Berk.

Molecular Weight:256.06
XLogP3:2.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:254.9159841
Monoisotopic Mass:254.9159841
Topological Polar Surface Area:88.3
Heavy Atom Count:14
Complexity:320
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes