Ethyl chloroformate → HCID 4095742, compound

Ethyl chloroformate 5.0 mL, 52 mmol) was added to a stirred mixture of N,N-diethyl-p-phenylenediamine hydrochloride (10 g, 50 mmol) and sodium hydrogen carbonate (23.0 g) in dichloromethane (120 mL) at room temperature under nitrogen. After four days at room temperature, the precipitate which had formed was removed by filtration through a pad of celite. The solid residue was washed with dichloromethane and the combined dichloromethane extracts were concentrated to produce a black oil, which was redissolved in dichloromethane (110 mL) and stirred with silica (100 cc) for 30 minutes. The silica was then removed by filtration through celite. The residue was washed with additional dichloromethane (3×30 mL) and the combined dichloromethane extracts were concentrated to give N-ethoxycarbonyl-4-diethylaminoaniline (8.55 g, 73% yield) as a pale gray solid which melted at 31°-33° C. The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy.

1. customthe precipitate which had formed
2. customwas removed by filtration through a pad of celite
3. washThe solid residue was washed with dichloromethane
4. concentrationthe combined dichloromethane extracts were concentrated
5. customto produce a black oil, which
6. customThe silica was then removed by filtration through celite
7. washThe residue was washed with additional dichloromethane (3×30 mL)
8. concentrationthe combined dichloromethane extracts were concentrated

ORD record

ord-47d8e8e7e7b546e78d1dc983768a7607

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05236884