Iodine → HCID 10150159, compound

Participants

Reaction Conditions

Reaction Steps

Phenothiazine (2.0 g, 10 mmole) and 4-aminobenzotrifluoride (1.77 g, 11 mmole) were dissolved in methanol (MeOH) (100 mL) with warming to 45° C., treated with a solution of I2 (5.0 g, 19.4 mmole) in MeOH (80 mL) in one portion and allowed to stir for 3 h at 45° C. The reaction mixture was filtered and the collected solid was washed with MeOH (100 mL). The solid was dissolved in CHCl3 (60 mL) containing triethylamine (NEt3) (6 mL) then this solution was diluted with hexane (200 mL) and chilled in an ice bath for 2 h. The purple solid that separated was collected by filtration and redissolved in CHCl3 /NEt3 (10:1, v:v) (50 mL) and chromatographed on silica gel (250 g) using CHCl3 /acetone (96:4, v:v) development. The purple product band was collected and evaporated to dryness in vacuo to afford 4 (0.26 g, 7.3%) with mp=207°-8° C.

Provenance & Evidence