Hexane → HCID 25029879, compound

Participants

Reaction Conditions

Reaction Steps

N,N-diisopropylethylamine (1.0 mL, 5.7 mmol) was added dropwise to a solution of 2-{[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amino}-2-methylpropan-1-ol (0.7 g, 2.4 mmol), prepared in the previous step, in 20 mL of dry methylene chloride at 0° C., followed by triphosgene (0.8 g, 2.8 mmol) in 20 mL of dry dichloromethane. The orange solution was stirred at 0° C. for 3 h, and then allowed to warm to room temperature. TLC (3:1 hexane:ethyl acetate) indicated the reaction was complete. The reaction was washed with 2N HCl and the aqueous layer was extracted with methylene chloride. The combined organic layer was dried (anhydrous MgSO4), filtered and concentrated under reduced pressure to give 900 mg of a yellow solid. Purification of the solid on silica gel using a stepwise gradient of 6:1 to 5:1 hexane:ethyl acetate gave the title compound (268 mg, 35%), mp 176-179° C.

Provenance & Evidence