Triphenylphosphine → 1-(7-Vinyl-2-benzothiazolyl)-3-ethylurea

Participants

Reaction Conditions

Reaction Steps

Similar to the synthesis of Example 203, a mixture of 1-(7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea (0.050 g, 80% pure, 0.11 mmol), lithium chloride (0.039 g, 0.92 mmol, 8.4 eq), triphenylphosphine (0.017 g, 0.066 mmol, 0.6 eq), Pd(PPh3)2Cl2 (0.009 g, 0.013 mmol, 0.12 eq), tetravinyltin (0.040 mL, 0.22 mmol, 2.0 eq), and a crystal of 2,6-di-tert-butyl-4-methylphenol was purged with nitrogen gas, and was heated at about 100° C. for about 1.5 hours. The mixture was taken up in MeOH, filtered, concentrated, and purified by HPLC and preparative TLC in ethyl acetate/heptane mixture to obtain 0.004 g (14%) of the desired compound. LC/MS 248 (M+1); LC retention time 2.96 min.

Provenance & Evidence