2-chloro-5-cyanobenzenesulfonyl chloride

2-chloro-5-cyanobenzenesulfonyl chloride - Names and Identifiers

Name	2-chloro-5-cyanobenzene-1-sulfonyl chloride
Synonyms	2-Chloro-5-Cyanobenzenesulfonyl Chloride 2-chloro-5-cyanobenzenesulfonyl chloride Benzenesulfonyl chloride, 2-chloro-5-cyano- 2-chloro-5-cyanobenzene-1-sulfonyl chloride
CAS	942199-56-6
InChI	InChI=1S/C7H3Cl2NO2S/c8-6-2-1-5(4-10)3-7(6)13(9,11)12/h1-3H

2-chloro-5-cyanobenzenesulfonyl chloride - Physico-chemical Properties

Molecular Formula	C7H3Cl2NO2S
Molar Mass	236.08
Density	1.65
Storage Condition	under inert gas (nitrogen or Argon) at 2-8°C

2-chloro-5-cyanobenzenesulfonyl chloride - Reference Information

preparation

commercially available 4-chloro-3-benzonitrile was dissolved in 4 parts of THF. Sodium hydrosulfide (3 eq) was added to one portion of water and stirred overnight at 45 °c. TLC(25% EtOAc in hexanes) confirmed the completion of the reaction. THF was evaporated in vacuo and the product precipitated. The white solid was collected by vacuum filtration, washed with water and dried in a vacuum oven with gentle heating (97.0% yield). The aniline product was ground in a mortar and pestle and dissolved in a mixture of 11 parts of HCl and 4 parts of acetic acid. In another vessel, 50 parts of acetic acid were stirred with SO2 gas until saturation (confirmed by weight). The triacetic acid: aniline mixture was placed in a dry ice/ethanol bath at 10 °c. Sodium nitrite (1.1 equivalents) was dissolved in a minimum amount of water and added dropwise to the HCl salt: aniline mixture without allowing the temperature to rise above about -5 °c. The resulting mixture was stirred for 45 minutes to form diazonium ions. Copper (I) chloride (0.1 equivalents) and copper (II) chloride (0.25 equivalents) were added to the SO2/acetic acid solution and stirred for 30 minutes and cooled to 10 °c in an ice bath. The diazo mixture was added to copper (I) chloride in portions In the suspension of copper (II) chloride, the temperature is maintained at 30 ° C. Or lower. Once fully mixed, the mixture was stirred until gas evolution ceased, forming a dark green solution. The mixture was then poured slowly into 200 parts of ice-water with stirring until the ice had melted. The resulting white precipitate 2-chloro-5-cyanobenzene-1-sulfonyl chloride was collected by vacuum filtration and washed with water (72.9% yield).

Application

2-chloro-5-cyanobenzene-1-sulfonyl chloride as Cyanogen derivatives, it can be used as a pharmaceutical synthesis intermediate.

Last Update：2024-04-09 15:16:53