Pyridine → Phenyl Methylcarbamate

Methylamine hydrochloride (16.9 g, 250 mmol) was dissolved in N,N-dimethylformamide (250 ml), pyridine (44 ml, 275 mmol) was added thereto, and the reaction mixture was stirred. The reaction mixture was cooled with ice, phenyl chloroformate (35 ml, 275 mmol) was added dropwise thereto, and the reaction mixture was then stirred at room temperature for 24 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained crystals were suspended in diethylether, diluted with hexane, filtered off, washed with the diethylether:hexane=1:1, and dried by evacuation, to yield the title compound (22.3 g, 147 mmol, 59.1%) as colorless crystals.

1. additionwas added dropwise
2. stirringthe reaction mixture was then stirred at room temperature for 24 hours
3. customThe reaction mixture was partitioned between ethyl acetate and water
4. washThe organic layer was washed with brine
5. dry with materialdried over anhydrous magnesium sulfate
6. distillationthe solvent was distilled off under reduced pressure
7. additiondiluted with hexane
8. filtrationfiltered off
9. washwashed with the diethylether
10. dry with materialhexane=1:1, and dried by evacuation

ORD record

ord-ca42d9efd0934f719278705902402519

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07468380B2