N-Methoxy-N,2-dimethylpropanamide Chemical Properties

Boiling point:

137.7±23.0 °C(Predicted)

Density 

0.945±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, DCM, Ethyl Acetate

form 

Oil

color 

Colourless

Safety Information

HS Code 

2928009090

N-Methoxy-N,2-dimethylpropanamide Usage And Synthesis

Uses

N-Methoxy-N-methylisobutyramide is an intermediate in the synthesis of pteridine derivatives with potential protective effects with vibrio cholerae infection.

Synthesis

I. Synthesis of N-methoxy-N,2-dimethylpropionamide. Isobutyryl chloride (6.02 mL, 57.5 mmol) was added slowly and dropwise to a solution of N,O-dimethylhydroxylamine hydrochloride (5.61 g, 57.5 mmol) and triethylamine (17.6 mL, 126.5 mmol) in dichloromethane (100 mL). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was washed with deionized water (100 mL) and the organic layer was dried with anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure and the crude product was purified by silica gel column chromatography (eluent: n-hexane to 9:1 n-hexane/ethyl acetate) to afford N-methoxy-N,2-dimethylpropanamide (5.55 g, 74% yield).1H NMR (300 MHz, DMSO-d6) δ 3.72 (s, 3H), 3.31 (m, 1H), 3.18 (s, 3H) 1.09 (d, J = 6.87 Hz, 6H).

References

[1] Organic Letters, 2012, vol. 14, # 9, p. 2250 - 2253
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 7, p. 3117 - 3130
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 4840 - 4860
[4] Chemistry - A European Journal, 2017, vol. 23, # 57, p. 14345 - 14357
[5] Organic and Biomolecular Chemistry, 2013, vol. 11, # 20, p. 3337 - 3340

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