Methyl iodide → HCID 15042514, compound

1.57 g (4.54 mmol) of 4,5-di(2-methoxyethoxymethoxy)-2-nitroaniline obtained in step (C) of Reference Example 34 was dissolved in 16 ml of N,N-dimethylformamide, and 2 g (8.63 mmol) of silver oxide and 10 ml (160 mmol) of methyl iodide were added thereto. The mixture was stirred at room temperature for one hour. The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (Wakogel C-300, ethyl acetate/hexane=1/1). The eluted fraction containing the desired compound was concentrated to obtain 0.85 g of crude 4,5-di(2-methoxyethoxymethoxy)-N-methyl-2-nitroaniline. (B) 0.85 g of the crude product obtained in the above reaction (A) was dissolved in 16 ml of ethanol, and 0.4 g of a 10% palladium carbon catalyst was added thereto. The catalytic hydrogenation was conducted at 80° C. for two hours. The catalyst was removed by filtration, and then to the filtrate, 1 g (6.25 mmol) of potassium O-ethyl dithiocarbonate was added. The mixture was refluxed at a boiling point for two hours. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in water. The solution was adjusted to pH5.0 with acetic acid and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (Wakogel C-300, ethyl acetate/hexane=3/1) to obtain 67 mg of the above-identified compound.

1. distillationThe solvent was distilled off under reduced pressure
2. additionThe eluted fraction containing the desired compound
3. concentrationwas concentrated

ORD record

ord-e57f6d911ac74b6ca291b6fd4b8c3d4b

Source dataset

uspto-grants-1993_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05225406