Acetonitrile → HCID 53482827, compound

To a flame-dried 25 mL round-bottom flask equipped with a magnetic stirring bar was added m-toluidine (365 mg, 3.4 mmol), o-tolualdehyde (391 mg, 3.3 mmol) and 5 mL of dry acetonitrile. The solution was stirred to make a homogeneous solution, then trimethylsilyl cyanide (480 μL, 3.6 mmol) was added and the solution stirred at room temperature for 23 h. The reaction was quenched by adding 5.5 mL satureated ammonium chloride solution and allowed to vent. The reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and concentrated to give the crude product (50% dichloromethane/hexanes, Rf=0.025). The crude was dissolved in a minimal amount of boiling toluene, a 4-5 fold volume of hexanes added and the solution allowed to sit for several hours, filtered, and dried to give XXX (531 mg, 68.1% yield) as a crystalline solid. Approximately 400 mg of the recrystallized material was additionally purified by flash chromatography using 50% dichloromethane/hexanes, which, after concentration, gave XXX as a white crystalline solid (m.p. 103-104° C.).

1. customTo a flame-dried 25 mL round-bottom flask equipped with a magnetic stirring bar
2. stirringthe solution stirred at room temperature for 23 h
3. customThe reaction was quenched
4. additionby adding 5.5 mL
5. extractionThe reaction mixture was extracted with ethyl acetate
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customto give the crude product (50% dichloromethane/hexanes, Rf=0.025)
10. waitto sit for several hours
11. filtrationfiltered
12. customdried

ORD record

ord-9828677727064f8b9567dd9d780fbaff

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329756B2