Hydrochloric Acid → HCID 19785567, compound

Participants

Reaction Steps

To a solution of ethyl 4-(1-(2-fluoro-4-biphenylyl)-ethyl)-2-methylamino-5-thiazolecarboxylate (3.55 g, 9.23 mmoles) and methyl iodide (2.81 g, 18.8 mmoles) in benzene (70 ml) were added 50% aqueous solution of sodium hydroxide (35 ml) and tetra-n-butylammonium hydrogen sulfate (3.13 g, 9.22 mmoles) and the resulting mixture was stirred at room temperature for 5.5 hours. The reaction mixture was diluted with water, acidified to pH 6 with 1M hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. Purification of the residue by means of silica gel column gave the desired ethyl 4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-dimethylamino-5-thiazolecarboxylate (3.68 g, 9.23 mmoles, quantitative yield) as a colorless oil.

Provenance & Evidence