Methyl iodide → HCID 18519604, compound

Participants

Reaction Steps

Step 2 To a suspension of sodium hydride (1.23 g) in N,N-dimethylformamide (70 ml) was added dropwise a solution of ethyl 3-amino4,4,4-trifluorocrotonate (5.6 g) in toluene (50 ml) at 0° C. under nitrogen atmosphere. After 30 minutes, a solution of 4-chloronaphthyl isocyanate (28 mmol) in a mixed solvent of N,N-dimethylformamide (30 ml) and toluene (50 ml) was added dropwise at same temperature. The resulting solution was stirred for 2 hours at ambient temperature, and then methyl iodide (8 g) was added. After 12 hours, the reaction mixture was partitioned with water(200 ml) and a mixed solvent of ethyl acetate-hexane (1:1, 300 ml). The organic phase was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and obtained solid was washed with hot ethyl acetate to give 3-(4-chloronaphthalen-1-yl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidindione (6.6 g) as a brown solid.

Provenance & Evidence