Dimethylcarbamoyl Chloride → HCID 17862041, compound

To a suspension of sodium hydride (5.74 g, 239 mmol), which was prepared free from mineral oil by washing with hexane, in dimethylformamide (100 ml) was added 2,4-dihydroxybenzaldehyde (15.0 g, 109 mmol) at 0° C. with stirring, and the resulting mixture was stirred for 30 minutes at 0° C. under a nitrogen atmosphere. Subsequently, N,N-dimethylcarbamoyl chloride (10.1 ml, 110 mmol) was added at 0° C., and the resulting mixture was stirred for 2 hours at room temperature under a nitrogen atmosphere. After stirring, water (300 ml) was added to the reaction mixture, and the resulting mixture was washed with ethyl acetate (200 ml×1). The aqueous layer was acidified to pH 1 with concentrated hydrochloric acid and extracted with ethyl acetate (200 ml×3). The extract was washed successively with water (300 ml×3) and saturated aqueous sodium chloride solution (200 ml×2), dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to afford the crude product. The crude product was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (5:1-1:2) as the eluent to afford the title compound (6.78 g, yield: 30%) as a colorless solid.

1. customwas prepared free from mineral oil
2. washby washing with hexane, in dimethylformamide (100 ml)
3. stirringthe resulting mixture was stirred for 30 minutes at 0° C. under a nitrogen atmosphere
4. stirringthe resulting mixture was stirred for 2 hours at room temperature under a nitrogen atmosphere
5. stirringAfter stirring
6. washthe resulting mixture was washed with ethyl acetate (200 ml×1)
7. extractionextracted with ethyl acetate (200 ml×3)
8. washThe extract was washed successively with water (300 ml×3) and saturated aqueous sodium chloride solution (200 ml×2)
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationfiltered
11. customevaporated in vacuo
12. customto afford the crude product
13. customThe crude product was purified by chromatography on a silica gel column

ORD record

ord-29aa1a9678cd44989c0fb030e2ab7175

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504437B2