Methyl iodide → 5-(N-formyl-N-methylamino)-1-methylpyrazole

To a solution of 5-formamido-1-methylpyrazole in N,N-dimethylformamide (50 ml) was sodium hydride (1.6 g) under ice-cooling. Then, to the mixture was added methyl iodide (2.5 ml) at the same condition. The mixture was stirred for 1 hour under ice-cooling. To the reaction mixture was added a mixture of ethyl acetate (500 ml) and water (100 ml). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (50 ml×2). The organic solution was dried over magnesium sulfate. The solvent was distilled off and the residue was subjected to a column chromatography on silica gel using a mixture of ethyl acetate and diisopropyl ether (3:1) as an eluent. Fractions containing the object compound were collected and evaporated in vacuo to give 5-(N-formyl-N-methylamino)-1-methylpyrazole (2.5 g).

1. temperaturecooling
2. temperaturecooling
3. additionTo the reaction mixture was added
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with ethyl acetate (50 ml×2)
6. dry with materialThe organic solution was dried over magnesium sulfate
7. distillationThe solvent was distilled off
8. additiona mixture of ethyl acetate and diisopropyl ether (3:1) as an eluent
9. additionFractions containing the object compound
10. customwere collected
11. customevaporated in vacuo

ORD record

ord-ea9e1aaa7a704baeb11b1cd0521584d0

Source dataset

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05663163