2-Nitro-4-(trifluoromethyl)benzamide → 4'-(2,2,2-trifluoroethoxy)-7-(trifluoromethyl)-1H-spiro[quinazolin-2,1'-cyclohexan]-4(3H)-one

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Reaction Steps

2-Nitro-4-trifluoromethylbenzamide (347 mg, 1.47 mmol), 4-(2,2,2-trifluoroethoxy)cyclohexanone (303 mg, 1.54 mmol) and tin(II) chloride hydrate (663 mg, 2.94 mmol) were added to toluene (5 ml) under argon and stirred under reflux conditions for 10 h. After cooling to room temperature, filtration with suction and thorough drying of the solid which precipitated gave 4′-(2,2,2-trifluoroethoxy)-7-(trifluoromethyl)-1H-spiro[quinazolin-2,1′-cyclohexan]-4(3H)-one (223 mg, 36% of theory) as a colorless solid. 1H NMR (400 MHz, d6-DMSO δ, ppm) 8.23 (br. 5, 1H, NH), 7.73 (d, 1H), 7.21 (br. s, 1H, NH), 7.19 (s, 1H), 6.90 (d, 1H), 4.06 (q, 2H), 3.51 (m, 1H), 1.90 (m, 4H), 1.62 (m, 4H).

Provenance & Evidence