Cyanamide → HCID 89768781, compound

Participants

Reaction Steps

At RT, 234 mg (5.56 mmol) of cyanamide and 1.06 g (5.96 mmol) of N-bromosuccinimide were added in succession to a solution of 1.14 g (3.27 mmol) of 2-methoxy-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide and 440 mg (3.92 mmol) of potassium tert-butoxide in 70 ml of methanol. The contents were then stirred at RT for 16 h. For work-up, the mixture was freed from the solvent on a rotary evaporator at a temperature of at most 30° C. The residue was stirred in a mixture of 150 ml of ice-cold dichloromethane and 50 ml of ice-cold aqueous 10% by weight strength sodium bisulfate solution for about two minutes. After phase separation, the aqueous phase was extracted with 50 ml of dichloromethane. On a rotary evaporator, the combined organic phases were freed from the solvent. The residue was taken up in 60 ml of acetonitrile and 60 ml of water. 1.57 g (9.80 mmol) of sodium permanganate monohydrate were then added. The reaction mixture was stirred at RT for four days. For work-up, aqueous 10% by weight strength sodium bisulfate solution was added. Water was then added, and the mixture was extracted three times with dichloromethane. On a rotary evaporator, the combined organic phases were freed from the solvent at a temperature of at most 30° C. The residue was purified chromatographically, which gave 40 mg of 3-(N-cyano-S-methylsulfinimidoyl)-2-methoxy-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide and 650 mg of 3-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide.

Provenance & Evidence