Diphenyl carbonate → Methyl 4-iodo-2-(3-(4-methoxy-6-methyl-1,3,5-triazine-2-yl)ureidosulfonyl)benzoate

Participants

Reaction Conditions

Reaction Steps

5.09 g of sodium tert-butylate was added to a suspension of 3.69 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 100 ml of DMA at room temperature. After cooling to 3-7° C., a solution of 5.64 g of diphenyl carbonate and 50 ml of DMA was added dropwise, to form a reaction mixture. The reaction mixture was then stirred at that temperature for 15 minutes. The reaction mixture was then added dropwise to a solution of 8.85 g of methyl 2-aminosulfonyl-4-iodobenzoate and 50 ml of DMA at 3-7° C., to form a resulting mixture which was stirred at 3° C. for 1 hour and at room temperature for 2 hours. The volatile components were then distilled off under reduced pressure. The residue was dissolved in 250 ml of water and acidified with concentrated hydrochloric acid (pH=2-3) whereby the crude product separated out. The crude product which separated out was washed with methanol and diisopropyl ether. After drying, 8.4 g of the desired product (purity>92%) was obtained.

Provenance & Evidence