Methylamine → N-Methyl-6-nitrobenzo[D]thiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

methanamine (0.793 mL, 19.30 mmol), 2-bromo-6-nitrobenzo[d]thiazole (1 g, 3.86 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.268 g, 0.46 mmol), cesium carbonate (1.886 g, 5.79 mmol) and diacetoxypalladium (0.043 g, 0.19 mmol) were suspended in 1,4-dioxane (8 mL) and sealed into a microwave tube. The reaction was heated to 150°C for 30 minutes in the microwave reactor and cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and pure fractions were evaporated to dryness to afford a crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 50% DCM in EtOAc. Pure fractions were evaporated to dryness to afford N-methyl-6-nitrobenzo[d]thiazol-2-amine (0.050 g, 6.19 %) as a yellow solid.

Provenance & Evidence