Phenylacetaldehyde → Dimethyl[2-(prop-2-yn-1-yloxy)ethyl]amine

Participants

Reaction Conditions

Reaction Steps

To a solution of the phenyl-acetaldehyde 1a or 2-nitro-phenyl-acetaldehyde 1b (8.3 mmol), thiosemicarbazide 2b (0.757 gr, 8.32 mmol) in H2O-methanol 55 ml (1:10 v/v) were added NaCN (0.624 g, 12.7 mmol) and NH4Cl (1.04 g, 19.44 mmol). The reaction mixture was stirred overnight at 50° C. The product from 1b was filtered, washed with cold water and dried under vacuum yielding 0.157 g (10%) of pure hydrazinecarbothioamide (3b). The precipitated crude product from 1a was purified on C18-reversed phase flash chromatography column employing a linear gradient of 0-30% A in B (flow-rate 40 mL/min), where A is 0.1% formic acid in CH3CN and B is 0.1% of formic acid in water, yielding 310 mg (15%) of pure 3b.

Provenance & Evidence