Ethyl N-[[(2,4,6-trimethylphenyl)sulfonyl]oxy]ethanimidate

white to light yellow crystalline powder

A solution of ethyl N-hydroxyacetimidate (2.00 g, 19.4 mmol), N, N-diisopropylethylamine (3.01 g, 23.3 mmol) and 4-dimethylaminopyridine (240 mg, 1.96 mmol) in anhydrous dichloromethane (30 mL) was cooled to 0 °C. To this cold solution 2, 4, 6-trimethylbenzene-1-sulfonyl chloride (4.66 g, 21.3 mmol) was added slowly, warmed to room temperature and stirred for 1 hour. The reaction was quenched with the addition of water (40 mL) and this mixture was extracted with dichloromethane (30 mL, 3 times). The combined dichloromethane layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The crude obtained was purified by silica flash column chromatography with 5percent ethyl acetate in hexanes as the eluent to obtain 9 as white solid (5.19 g, 94percent). Ethyl N-hydroxyacetimidate (10.3 g, 47 mmol, 1.1 eq) and triethylamine (25.5 ml, 94 mmol, 2 eq) were dissolved in DMF (40 ml, 2 vol) and the mixture cooled to 0 °C. O-mesitylene chloride (20 g, 47 mmol, 1 eq) was then added portionwise and the mixture stirred at 0 °C for 45 minutes. The above solution was poured into ice water, and solid obtained was filtered and washed with water. Yield : 23 g (92 percent). Into a 500mL reaction flask added ethyl acetohydroxamate (71g, 0.5mol, 1.0eq) and ethanol (284mL, 4P) to form into an ethanol solution of ethyl acetohydroxanoate, into ethyl acetohydroxanoate ethanol solution added sodium hydroxide (24g, 0.6mol, 1.2eq), added the drops of 2, 4, 6-trimethylbenzenesulfonyl chloride (120.3g, 0.55mol, 1. 1eq), magnetic stirring speeds up the reaction, the reaction temperature is controlled between 15-25 ° C, after the addition is completed, the temperature is maintained between 15-25 ° C for 2 hours, reaction solution added into water (284mL, 4P), the precipitated solid is suction filtered, and then obtained filter cake is washed with ethanol, obtained solid is dried and then obtained 244g of ethyl O-(2, 4, 6-trimethylbenzenesulfonyl)acetohydroxamate, yield is 87percent0-(mesityIsulfonyl)hydroxyIamne. Ethyl N-hydroxyacetimidate (10.3 g, 47 mmol, 1.1 eq) and triethylamine (25.5 ml, 94 mmol, 2 eq) were dissolved in DMF (40 ml, 2 vol) and the mixture cooled to 0

Molecular Weight:285.36
XLogP3:3.3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:285.10347926
Monoisotopic Mass:285.10347926
Topological Polar Surface Area:73.3
Heavy Atom Count:19
Complexity:401
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes