Pyridine → HCID 16451276, compound

Methyl 4-aminobenzoate (Aldrich, 5.0 g, 33 mmol) was dissolved in 120 mL of anhydrous methylene chloride containing pyridine (3.2 mL, 39.6 mmol), and dimethylaminopyridine (DMAP, 500 mg) was added. To the ice-cooled mixture was added dimethylcarbamyl chloride (3.34 mL, 36.3 mmol) while stirring. The stirring was continued for 16 h at room temperature. The reaction was quenched with water (50 mL) and the organic layer separated. The aqueous layer was extracted with chloroform (50 mL). The combined organic extract was dried over sodium sulfate. The volatiles were evaporated on a rotoevaporator to give a residue, which was applied to a column of silica gel (2 cm dia, 16.5 cm high, 42 g). Chloroform (1.2 L) eluted the starting material (3 g) while the desired material was washed with 1% methanol in chloroform (700 mL) and crystallized from chloroform-methanol-hexane. The white solid was separated, dried in air followed by drying in a pistol at acetone reflux in vacuo to give 885 mg (30% based on starting material consumed) of methyl 4-(N,N-dimethylcarbamyl)aminobenzoate, mp 169°-170° C.

1. additionwas added
2. customThe reaction was quenched with water (50 mL)
3. customthe organic layer separated
4. extractionThe aqueous layer was extracted with chloroform (50 mL)
5. extractionThe combined organic extract
6. dry with materialwas dried over sodium sulfate
7. customThe volatiles were evaporated on a rotoevaporator
8. customto give a residue, which
9. washChloroform (1.2 L) eluted the starting material (3 g) while the desired material
10. washwas washed with 1% methanol in chloroform (700 mL)
11. customcrystallized from chloroform-methanol-hexane
12. customThe white solid was separated
13. customdried in air
14. dry with materialby drying in a pistol at acetone
15. temperaturereflux in vacuo

ORD record

ord-6097ffbd7ca547678f665fee61419084

Source dataset

uspto-grants-1997_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05602277