Triethylamine → 1-(6-Trimethylsilylacetylenyl-2-benzothiazolyl)-3-ethylurea

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(6-bromo-2-benzothiazolyl)-3-ethylurea (0.100 g, 0.33 mmol), Pd(PPh3)2Cl2 (0.012 g, 0.017 mmol, 0.05 eq), and triethylamine (0.20 mL, 1.42 mmol, 4.3 eq) in 1 mL of anhydrous DMF was bubbled with nitrogen gas for about 5 minutes, followed by the addition of trimethylsilyl acetylene (0.23 mL, 1.65 mmol, 5.0 eq). The mixture was heated at about 80° C. with stirring in a sealed tube for about 15 hours. The mixture was cooled down, taken up in 10 mL MeOH, and evaporated to dryness. Purification by HPLC gave pure desired compound 0.093 g (89%). LC/MS 318 (M+1); LC retention time 3.77 min.

Provenance & Evidence