Sodium Hypochlorite → 2-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamate

To a solution obtained by adding 1,2-hydrazinedicarboxylic acid bis(2-methoxyethyl) ester (200 mg, 0.85 mmol) and toluene (2 mL) to a 10 mL flask, followed by cooling with an ice bath, was added dropwise a 5% sodium hypochlorite solution (1.39 g, 0.85 mmol), and the reaction was allowed to proceed for one hour. After the reaction, the solution was washed with water (1 mL, ×2), and dehumidified with anhydrous magnesium sulfate, followed by concentration to dryness. The resulting solid was recrystallized with toluene (1 mL) and hexane (5 mL), to give azodicarboxylic acid bis(2-methoxyethyl) ester as a pale yellow crystal (73 mg, yield: 37%).

1. customTo a solution obtained
2. temperatureby cooling with an ice bath
3. customAfter the reaction
4. washthe solution was washed with water (1 mL, ×2)
5. concentrationfollowed by concentration to dryness
6. customThe resulting solid was recrystallized with toluene (1 mL) and hexane (5 mL)

ORD record

ord-26f20dc7d4574b2ba5fcb028ba9e9038

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947816B2