Nitrogen → Methyl 2-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)thiazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methyl 2-(chloromethyl)thiazole-4-carboxylate (S. A. Hermitage et al. Organic Process Research & Development, 5, 37-44, 2001) (2.05 g, 10.7 mmol) in DMF (20.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (T. E. Eagles et al. Organic preparations and procedures 2 (2), 117-119, 1970; P. N. Neuman J. Heterocycl. Chem. 8, 51-56, 1971) (11.53 g of a 8% solution in DMF, 9.70 mmol) in DMF (20.0 mL) pre-treated for 30 min with DIPEA (3.21 mL, 19.4 mmol) and the reaction mixture was stirred overnight at 50° C. Water (50 mL), followed by EA (50 mL) was added. The layers were separated and the aq. layer was extracted with EA (2×50 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (gradient from 60:40 hept-EA to 50:50 hept-EA)) gave the title compound as a yellow solid. TLC: rf (6:4 hept-EA)=0.31. LC-MS-conditions 07: tR=0.67 min, [M+H]+=270.21.

Provenance & Evidence