Chlorosuccinimide → N-Hydroxy-4-isobutylbenzenecarboximidoyl chloride

To a solution of 4-isobutylbenzaldehyde oxime (1.0 g, 5.6 mmol) that was obtained in Example 9 (9e) in N,N-dimethylformamide (10 ml) was added N-chlorosuccinimide (0.15 g, 1.1 mmol) with stirring, and furthermore, a small amount of gaseous hydrochloric acid was bubbled into the resulting mixture under stirring, and then the resulting mixture was stirred at room temperature for 10 minutes. After repeating the series of the same procedures described above five times in total, the reaction mixture was poured into ice water (100 ml) and extracted with ether. The extract was washed successively with water and a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo to afford the title compound (1.2 g) in a yield of 100% as a yellow oily product.

1. customfurthermore, a small amount of gaseous hydrochloric acid was bubbled into the resulting mixture
2. stirringunder stirring
3. stirringthe resulting mixture was stirred at room temperature for 10 minutes
4. additionthe reaction mixture was poured into ice water (100 ml)
5. extractionextracted with ether
6. washThe extract was washed successively with water
7. dry with materiala saturated aqueous solution of sodium chloride and dried over magnesium sulfate
8. filtrationAfter filtration
9. customthe filtrate was evaporated in vacuo

ORD record

ord-27d681d9ca584b608e8c985b92411b3f

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687491B2