Dimethyl Sulfoxide → 3-[(2-Methoxyethoxy)carbonylamino]benzaldehyde

Temperature

-60 °C

To a mixture of 13 ml of oxalyl chloride and 400 ml of dichloromethane was added dropwise a solution of 23 ml of dimethyl sulfoxide in 40 ml of dichloromethane at −60° C. for 15 minutes. After stirred at −60° C. for 10 minutes, a solution of 30.2 g of 3-[(2-methoxyethoxy)carbonylamino]benzyl alcohol in 100 ml of dichloromethane was added dropwise at −60° C. for 25 minutes. After stirred at −60° C. for 20 minutes, 56 ml of triethylamine was added dropwise at −60° C. for 15 minutes. After stirred at room temperature for 45 minutes, water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed successively with water and then an aqueous saturated sodium chloride solution. After dried over anhydrous magnesium sulfate and then concentration, the resulting crude crystals were washed with t-butyl methyl ether and then dried to obtain 17.55 g of 3-[(2-methoxyethoxy)carbonylamino]benzaldehyde [Compound No. (h)] as a white solid.

1. stirringAfter stirred at −60° C. for 20 minutes
2. stirringAfter stirred at room temperature for 45 minutes
3. extractionfollowed by extraction with ethyl acetate
4. washThe organic layer was washed successively with water
5. dry with materialAfter dried over anhydrous magnesium sulfate
6. concentrationconcentration
7. washthe resulting crude crystals were washed with t-butyl methyl ether
8. customdried

ORD record

ord-f2c9df6d676e43c58c6a2c7ac31d7495

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989478B2