Pyridine → N,N-bis(4-methoxyphenyl)-2-oxopropanamide

Pyruvic acid (1.00 g, 11.34 mmol) was placed in a 250 mL three-necked round-bottomed flask fitted with a stirring bar, reflux condenser and a nitrogen inlet, and dissolved in 30 mL anhydrous THF at room temperature. Then, SOCl2 (2.03 g, 17.01 mmol) was added dropwise with stirring in 3 hours at room temperature. Bis(4-methoxyphenyl)amine (2.00 g, 8.72 mmol) was added under nitrogen protection. Pyridine (4.14 g, 52.3 mmol) were added to the mixture at 0° C. The reaction mixture was heated to reflux for 12 hours. The reaction was quenched by adding 30 mL of 2N HCl solution. The mixture was extracted with EtOAc (3×20 mL). The organic layers were separated, washed with brine (20 mL) and dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give a yellow residue. The solvent was removed and residue was subjected to flash column chromatography (silica gel, EtOAc/hexanes=3/7 v/v) to give a white solid product, N,N-bis(4-methoxyphenyl)-2-oxopropanamide, 2.15 g, 82.4% yield. MS: m/z 322 [M+Na]+.

1. customfitted with a stirring bar
2. temperaturereflux condenser and a nitrogen inlet
3. temperatureThe reaction mixture was heated
4. temperatureto reflux for 12 hours
5. customThe reaction was quenched
6. additionby adding 30 mL of 2N HCl solution
7. extractionThe mixture was extracted with EtOAc (3×20 mL)
8. customThe organic layers were separated
9. washwashed with brine (20 mL)
10. dry with materialdried over anhydrous MgSO4
11. customThe solvent was removed under reduced pressure
12. customto give a yellow residue
13. customThe solvent was removed

ORDレコード

ord-f4f649e9303449fcbbd1e04727cd0899

出典データセット

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08637706B2