반응 #2552

반응 방정식

o-anisidine

triethylamine

sodium hydroxide

4-chloromethylbenzoyl chloride

2-bromomethyl-1,3-dioxolan

→

title compound

수율 47.9%

4-Chloromethyl-N-(2-methoxyphenyl)-N-(1,3-dioxolan-2-yl)methylbenzamide

수율 47.9%

용매

methylene chloride

반응 조건

후처리

1. 1
   온도with cooling in an ice bath
2. 2
   workup.STIRRINGAfter 1 hour of stirring at the same temperature
3. 3
   추출the resulting mixture was extracted with methylene chloride
4. 4
   세척washed with 10% citric acid aqueous solution and saturated brine
5. 5
   건조dried on anhydrous sodium sulfate
6. 6
   기타Thereafter, the solvent was removed by evaporation
7. 7
   기타the resulting residue was purified

실험 절차

In an atmosphere of argon, a mixture consisting of o-anisidine (500 mg, 4.06 mmol), triethylamine (1.6 ml, 11.5 mmol) and 2-bromomethyl-1,3-dioxolan (0.96 ml, 8.18 mmol) was stirred at 80° C. for 4 days, dissolved in methylene chloride (8 ml) and then, with cooling in an ice bath, mixed with 20% sodium hydroxide aqueous solution (4 ml) and 4-chloromethylbenzoyl chloride (768 mg, 4.06 mmol). After 1 hour of stirring at the same temperature, the resulting mixture was extracted with methylene chloride, washed with 10% citric acid aqueous solution and saturated brine and then dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by subjecting it to a silica gel column chromatography (ethyl acetate:hexane=2:5) to obtain 704 mg (47.9%) of the title compound in the form of colorless solid.

출처