1,1-Dimethylhydrazine → HCID 18696625, compound

Participants

Reaction Steps

The solids from Step B were dissolved in 100 mL of dry tetrahydrofuran. 1,1-Dimethylhydrazine (3 g, 50.0 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water and extracted twice with diethyl ether. The combined organic layers were then washed once with saturated aqueous NaCl solution and dried over magnesium sulfate. The solvent was removed under reduced pressure to give an oil. This oil was then dissolved in 200 mL methylene chloride and cooled to 0° C. at which temperature triphosgene (4.08 g, 13.7 mmol) was added. The reaction mixture was refluxed for 16 h, cooled to room temperature and washed once with water. The organic layer was then dried over magnesium sulfate and concentrated under reduced pressure to yield a crude oil which was purified by silica gel chromatography using 3:2/hexanes:ethyl acetate as the eluent to yield 2 g of the title compound of Step C, a compound of the invention, as a solid. 1H NMR (CDCl3 ; 300 MHz): δ 3.53 (s,3H), 6.8-6.9 (m,3H), 7.0-7.2 (m,4H), 7.3-7.4 (m,3H), 7.71 (dd,1H, J=1.9, 7.7 Hz), 8.27 (dd,1H, J=1.8, 4.9 Hz).

Provenance & Evidence