1,1-Dimethylhydrazine → HCID 67414770, compound

Temperature

100 °C

The obtained 1-pentyl-3,1-benzoxazin-2,4-(1H)-dione (0.301 g, 1.29 mmol) was dissolved in toluene (4 ml), N,N-dimethylhydrazine (0.10 ml, 1.32 mmol) was added, and the mixture was stirred at 100° C. for 2 hr. The reaction mixture was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give N′,N′-dimethyl-2-pentylaminobenzohydrazide (0.218 g, 0.87 mmol, yield 67%). This was dissolved in methanol (3 ml), 36% formalin (0.35 ml, 4.31 mmol), sodium cyanoborohydride (0.174 g, 2.62 mmol) and acetic acid (0.1 ml) were added, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was concentrated under reduced pressure, and ethyl acetate was added. The mixture was washed with water, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give an acylhydrazine compound N′,N′-dimethyl-2-(N-methyl-N-pentylamino)benzohydrazide (0.103 g, 0.39 mmol, yield 45%).

1. customThe reaction mixture was evaporated under reduced pressure
2. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate)

ORD record

ord-08c7222b3c084a69b44c73581ee8709a

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022072B2