Hydrochloric Acid → HCID 15907991, compound

Participants

Reaction Steps

Ethyl-2-[((Z)-1-oxo-9-octadecenyl)amino]-4-thiazoleacetate (4.00 g, 8.89 mmol), sodium hydroxide (0.79 g, 19.8 mmol) and tetrahydrofuran (50 mL) were combined and cooled in an ice bath under N2 atmosphere. Enough distilled water was added to the mixture to dissolve the hydroxide and provide a homogeneous solution. The reaction was kept at 0° C. for 2 h, then allowed to warm to room temperature and stirred overnight. 10% aqueous HCl solution was added to the mixture, and stirring continued for 1 h. Ethyl acetate and saturated aqueous brine solution were added to the mixture, and the organic phase was separated and dried over MgSO4. After filtration and concentration the crude dark amber oil was treated with ether, stirred for 0.5 h and the product was collected on a Buehner funnel and air dried to give 1.5 g of the title compound as a white solid, mp 106°-108.5° C.

Provenance & Evidence