Dimethylformamide → 3-Carboethoxymethyl-5-benzylidenerhodanine

Under an atmosphere of nitrogen, 4.2 ml of anhydrous N,N-dimethylformamide was added dropwise to 0.279 g of 3-carboxymethyl-5-benzylidenerhodanine (prepared as described in Example 1) at room temperature, and then 1.14 ml of methanol solution of 91.15 mg of tetramethylammonium hydroxide was added dropwise. After the mixture was stirred at room temperature for 20-30 minutes, 0.075 ml of ethyl bromide was added dropwise to the reaction mixture. The mixture was stirred at the same temperature for about 2 hours, and then concentrated under reduced pressure. The residue was diluted with 15 ml of water and extracted with ethyl acetate. The extract was washed with 50 ml of aqueous solution of sodium bicarbonate, 50 ml of water and 50 ml of aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from a mixture of ethyl acetate and n-hexane (1:3) to obtain 14 mg of the titled compound.

1. stirringThe mixture was stirred at the same temperature for about 2 hours
2. concentrationconcentrated under reduced pressure
3. additionThe residue was diluted with 15 ml of water
4. extractionextracted with ethyl acetate
5. washThe extract was washed with 50 ml of aqueous solution of sodium bicarbonate, 50 ml of water and 50 ml of aqueous solution of sodium chloride
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was recrystallized from a mixture of ethyl acetate and n-hexane (1:3)

ORD record

ord-515fe300fabe4282982376ddf3db2edc

Source dataset

uspto-grants-1984_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04464382