Preparation and application of diphenyl iodide chloride salt_Kain Industrial Additive

Background and overview^[1]

Diphenyl iodide chloride salt can be used as a pharmaceutical synthesis intermediate. If diphenyl iodide chloride salt is inhaled, move the patient to fresh air; if skin contact occurs, take off contaminated clothing, rinse the skin thoroughly with soap and water, and seek medical attention if you feel unwell; if contact with eyes , you should separate your eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse your mouth immediately, do not induce vomiting, and seek medical attention immediately.

Preparation^[1]

The preparation of diphenyl iodide chloride salt is divided into the following two steps:

Step 1: To a vigorously stirred solution of 2-iodobiphenyl (24.0g, 85.7mmol) in acetonitrile (210mL) at room temperature was added [hydroxy(tosyloxy)iodo]benzene (33.6g, 85.7 mmol). The reaction mixture was stirred at room temperature for 4 days. The reaction mixture was filtered with suction, and the filter cake was washed with Et2O (400 mL). The solid was dried under vacuum at room temperature to obtain diphenylsulfonate iodide salt (34.8 g, 90%).

Step 2: Add an aqueous solution of potassium chloride (34.2g, 459mmol) (177mL) to a solution of diphenylsulfonate iodide (17.1g, 38.0mmol) in formic acid (88%, 590mL) at 75°C. )). A thick white precipitate forms immediately. The reaction mixture was suction filtered while still warm, and the solid was washed with water (200 mL) and EtOAc (200 mL), then dried under vacuum at room temperature to give diphenyl iodide chloride salt (10.0 g, 84%).

Apply^[1]

Diphenyl iodide chloride can be used to prepare diphenyl iodide potassium nitrate. The specific steps are as follows: Add diphenyl iodide chloride (15.0g, 47.7mmol) to deionized water (666mL) at 95°C. ) to the vigorously stirred suspension was added a solution of silver nitrate (16.7 g, 98.3 mmol) in hot deionized water. The reaction mixture was treated with a solution of sodium nitrate (222 g, 2610 mmol) in hot deionized water (260 mL) and stirring was continued at 95 °C for 0.5 h. The reaction mixture was cooled to 5-10°C (ice water bath) and suction filtered through shark skin. The filter cake was suspended in deionized water (2.67L), then stirred and heated at 95 °C for 0.5 h. The hot reaction mixture was suction filtered through sharkskin to remove silver chloride and the hot filtrate (clear and colorless) was treated with sodium nitrate (129g). The diphenyl iodide nitrate salt immediately precipitated from the solution and was collected by suction filtration. The solid was dried under vacuum at 45-50°C to give potassium diphenyl iodide nitrate (15.6 g, 96%).

Main reference materials

[1] WO2015157145 ODONIUM ANALOGS AS INHIBITORS OF NADPH OXIDASES AND OTHER FLAVIN DEHYDROGENASES; FORMULATIONS THEREOF; AND USES THEREOF