Triethylamine → HCID 19384277, compound

Participants

Reaction Steps

To a stirred solution of 4-amino-2-(4,4-difluorobut-3-enylthio)benzoxazole (Compound No 80, Example 4B(iv), 255 mg) in dichloromethane (2 cm3) and propionyl chloride (102 mg) at the ambient temperature was added dropwise triethylamine (120 mg) and the reaction stirred for 31/2 hours, after which gc analysis indicated complete consumption of starting material. The reaction mixture was poured into ethyl acetate and water and the phases separated. The aqueous layer was extracted twice with ethyl acetate and the combined organic layers washed with water and brine and then dried (MgSO4). Filtration and evaporation under reduced pressure gave a brown oil. Purification by silica gel chromatography using 30% t-butyl methyl ether in hexane as the eluent gave 4-(1-oxopropylamino)-2-(4,4-difluorobut-3-enylthio)benzoxazole as a pale yellow oil (124 mg). 1H NMR (DMSO): δ8.28(1H,d); 7.97(1H, b); 7.24(1H,t); 7.16(1H,d); 4.32(1H, ddt); 3.33(2H,t); 2.55(4H,m); 1.29(3H,t).

Provenance & Evidence