4-(Methylsulfonyl)phenylhydrazine hydrochloride synthesis

Yield: 67.9%

Reaction Conditions:

Stage #1:4-methanesulfonylphenylamine with hydrogenchloride;sodium nitrite in water at -10; for 1 h;
Stage #2: with hydrogenchloride;tin(II) chloride dihdyrate in water at -10; for 1 h;

Steps:

1-1 (1-1) Synthesis Example 1 (Synthesis of Squarylium Compound G)
100 mL of hydrochloric acid was placed in a 500 mL four-necked flask,The temperature inside the flask was cooled to -10 ° C. or lower in an ice water bath,While keeping the temperature in the flask not to exceed -10 ° C.,4- (methylsulfonyl) aniline 10.27 g(0.06 mol) were added and dissolved.After the fever ceased,While maintaining the temperature in the flask below -10 ° C.,4.47 g (0.065 mol) of sodium nitrite,In 30 g of distilled water was added dropwise over 1 hour.After completion of the dropwise addition, 67.7 g of tin chloride.dihydrate(0.30 mol) in 60 mL of hydrochloric acid,Was added dropwise over 1 hour while maintaining the temperature in the flask at -10 ° C. or lower, and the reaction proceeded.After completion of the reaction, the cake obtained by filtration was dried at 60 ° C. using a vacuum drier 12Dry for a while,4- (Methylsulfonyl) phenylhydrazine hydrochloride(Intermediate G1) was obtained.The yield based on 4- (methylsulfonyl) aniline was 67.9 mol%.

References:

Nippon Shokubai Co.;Hiranai, Tatsushi;Aoki, Masanori JP2018/95798, 2018, A Location in patent:Paragraph 0081; 0084