N-(3-METHOXYPHENYL)-2,2-DIMETHYLPROPANAMIDE Chemical Properties

Melting point:

125-126°C

Boiling point:

358.2±25.0 °C(Predicted)

Density 

1.057±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

14.66±0.70(Predicted)

Safety Information

HazardClass 

IRRITANT

HS Code 

2922290090

N-(3-METHOXYPHENYL)-2,2-DIMETHYLPROPANAMIDE Usage And Synthesis

Synthesis

Pivaloyl chloride (25.0 mL, 205 mmol) was slowly added dropwise at 0 °C under argon protection to a mixed solution of ethyl acetate (300 mL) and purified water (860 mL) containing m-aminoanisole (21.9 mL, 195 mmol), sodium carbonate monohydrate (62.0 g, 500 mmol). The reaction mixture was stirred at 0 °C for 1 h. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (300 mL). The organic layers were combined, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was recrystallized with ethyl acetate to afford N-(3-methoxyphenyl)pivalamide (Compound 1a) (40.2 g, 194 mmol, 99.5% yield) as a colorless solid.TLC showed Rf = 0.50 (hexane/ethyl acetate = 6:1).

References

[1] Journal of the American Chemical Society, 2004, vol. 126, # 4, p. 1150 - 1160
[2] Patent: EP2881397, 2015, A1. Location in patent: Paragraph 0053; 0054; 0055
[3] Patent: US2016/303089, 2016, A1. Location in patent: Paragraph 0161; 0162; 0163; 0164
[4] Patent: WO2004/103996, 2004, A1. Location in patent: Page 51
[5] Synlett, 2011, # 7, p. 1018 - 1022

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