Dimethylformamide → tert-butyl N-[N-[2-(2,4,6-trimethylphenyl)sulfanylacetyl]carbamimidoyl]carbamate

Participants

Reaction Steps

Mesitylthio acetic acid (6.90 g; 33 mmol), diisopropylethylamine (21.2 g; 164 mmol), tert-butyl amino(imino)methylcarbamate (6.37 g; 40 mmol), and 1-hydroxybenzotriazole monohydrate (6.13 g; 40 mmol) were dissolved in N,N-dimethylformamide (120 mL), 2-(1H)-benzotriazol-1-yl-1,1,3,3-tetramethyluronium hexafluorophosphate (15.2 g; 40 mmol) was added, and the mixture was stirred for 15 hours at room temperature. To the reaction solution, ethyl acetate (300 mL) was added, and the mixture was washed with 10% aqueous citric acid solution, brine, saturated aqueous sodium bicarbonate solution, and then brine. The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure to give 14.3 g of the title compound (yield 100%) as an oil.

Provenance & Evidence