ALPHA-CHLORO-4-NITROBENZALDOXIME

Synthesis of Compound YD-032YD-031 (887 mg, 5.3 mmol) was dissolved in anhydrousdimethylformamide (4.6 mL) and the solution was cooled to OYD-031 (887 mg, 5.3 mmol) was dissolved in anhydrous dimethylformamide (4.6 mL) and the solution was cooled to 0° C. N-Chlorosuccinimide (800 mg, 6.0 mmol) was added portion-wise with stirring. The cooling bath was removed and the resulting mixture was stirred at room temperature for 4 hours. Upon completion, ice water (20 mL) was added and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water 3 times and saturated brine once, and dried over magnesium sulfate. Removing the solvent after filtration afforded a white solid of YD-032 (1.064 g, 100percent). In an oven-dried flask 4-nitrobenzaldheyde oxime 26 (1.86g, 1.0equiv) was dissolved in 10mL of anhydrous N, N-dimethylformamide. 0.3g of N-chlorosuccinimide (0.2equiv) were added and the reaction stirred for 10min at room temperature. The solution was purged with 20mL of HClTo a solution of compound 17 (50.0g, 301mmol, 1.0equiv) in DMF (250ml) was added N-chlorosuccinimide (52.3g, 391mmol, 1.3equiv) and stirred at rt for 5h. Following reaction completion DMF was removed under reduced pressure and the obtained material was dissolved in ethyl acetate, washed with water, brine, dried over sodium sulfate, and the solvent was removed under reduced pressure to obtain a crude solid that was purified by column using 1:9 Ethyl acetate:Pet ether to obtain 51g (84percent) white solid compound. (0028)

Molecular Weight:200.58
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:199.9988697
Monoisotopic Mass:199.9988697
Topological Polar Surface Area:78.4
Heavy Atom Count:13
Complexity:218
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes