Methanamine, N-methoxy-, hydrochloride (1:1) → N-Methoxy-N-methyloxazole-4-carboxamide

Temperature

0 °C

To a suspension of methoxy-methylamine hydrochloride (2.3 g, 23.6 mmol) in 30 mL of dichloroethane at 0° C. was added dropwise 11.8 mL (23.6 mmol) of trimethylaluminum. The mixture was stirred at 0° C. for 20 min, and methyl 4-oxazolecarboxylate (1 g, 7.9 mmol) in 20 mL of dichloroethane was added in one portion. The mixture was poured into an ice-cold solution of 0.5N HCl/methylene chloride (2:1) and stirred for 10 min. The aqueous layer was extracted with methylene chloride (2×50 mL), and the combined organic layer was washed with saturated ammonium chloride solution, dried over sodium sulfate, and concentrated in vacuo. The resulting residue was purified by chromatography on silica (methylene chloride/ethyl acetate/methanol 6:3:1) to afford 1.0 g (81.9%) of 4-oxazolyl-N-methyl-N-methoxy-carboxamide.

1. stirringstirred for 10 min
2. extractionThe aqueous layer was extracted with methylene chloride (2×50 mL)
3. washthe combined organic layer was washed with saturated ammonium chloride solution
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated in vacuo
6. customThe resulting residue was purified by chromatography on silica (methylene chloride/ethyl acetate/methanol 6:3:1)

ORD record

ord-79ba21b5aefa4869bfc15ab596bd34e6

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05554620