Triethylamine → HCID 67468122, compound

Participants

Reaction Steps

To a suspension of N′-[(1Z)-2,2-dichloro-1-methylethylidene]-4-methylbenzenesulfonohydrazide (prepared according to WO2007088478 example 13) (5.0 g, 16.9 mmol) in methanol (100 mL), at 0° C. under an atmosphere of nitrogen, was added triethylamine (11.8 mL, 84.7 mmol, 5.0 eq.) over a period of 2 min. To the resulting orange solution was added a solution of 2-{[tert-butyl-(dimethyl)silyl]oxy}ethanamine (prepared according to J.O.C. 74(4), 1791-1793, 2009) (3.3 g, 18.8 mmol, 1.1 eq.) in methanol (70 ml). The reaction mixture was stirred at room temperature for 18 hr. The mixture was then evaporated under reduced pressure and the residue partitioned between tert-butyl methyl ether (250 mL) and aqueous citric acid (10% wt/vol, 100 mL). The organic phase was washed with aqueous sodium hydrogen carbonate (1M, 100 mL), saturated brine (20 mL) and dried over sodium sulphate. The resulting mixture was filtered and the filtrate concentrated under reduced pressure to give a crude brown oil. The crude oil was purified by chromatography on silica gel (200 g) eluting with a gradient of tert-butyl methyl ether in toluene (10:90 to 40:60) to give the title compound as a yellow oil (3.07 g, 75%).

Provenance & Evidence