1H-1,2,4-Triazole, 1-methyl- → N-methoxy-N,1-dimethyl-1H-1,2,4-triazole-5-carboxamide

Participants

Reaction Steps

A mixture of 1-methyl-1H-1,2,4-triazole (3.15 mL, 55.56 mmol) and methoxy(methyl)carbamic chloride (7.55 g, 61.11 mmol) in acetonitrile (60 mL) was cooled in an ice water bath before addition of TEA (8.52 mL, 61.11 mmol). The mixture was allowed to slowly warm to room temperature and was then stirred overnight. The material was diluted with ether and solids were filtered and rinsed well with ether. The filtrate was concentrated and the residue was taken up in ether. Insoluble solids were filtered off and rinsed well with additional ether. The filtrate was concentrated to give and oil that was chromatographed on silica gel (100% CH2Cl2 followed by gradient elution to 40% EtOAc in CH2Cl2) to afford product as an oil that slowly solidified. 6.13 g (65% yield).

Provenance & Evidence