Methylhydrazine → N,4-dimethylbenzenesulfonohydrazide

Into a 100 mL three necked round bottom flask equipped with a mechanical stirrer, thermometer, and dropping funnel under an atmosphere of nitrogen was added THF (25 mL), methylhydrazine (2.53 g, 2.92 mL, 55 mmol), and triethylamine (4.35 g, 5.99 mL, 55 mmol). The temperature of the mixture was lowered to approximately 5° C. and 4-methylbenzenesulfonyl chloride (9.5 g, 50 mmol) dissolved in 25 mL of THF was added dropwise at a rate such that the temperature did not rise over 10° C. The cooling bath was removed and the mixture was allowed to stir overnight at RT. Ether (100 mL) was added to the reaction mixture and the resulting slurry was washed with water (50 mL), brine (50 mL), dried (Na2SO4), and the solvent was removed in vacuo to give 9.5 g (95% yield) of the title product. 1H NMR (CDCl3) δ 7.7 (d, 2H), 7.4 (d, 2H), 3.6 (s, b, 2H), 2.8 (s, 3H), 2.4 (s, 3H)

1. customwas lowered to approximately 5° C.
2. additionwas added dropwise at a rate such that the temperature
3. customdid not rise over 10° C
4. customThe cooling bath was removed
5. additionEther (100 mL) was added to the reaction mixture
6. washthe resulting slurry was washed with water (50 mL), brine (50 mL)
7. dry with materialdried (Na2SO4)
8. customthe solvent was removed in vacuo

ORD record

ord-3441e79c14e7458faf15310c55ba3692

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06262305B1