2-methoxy-2-methylpropanamide synthesis

5synthesis methods

Product Name:2-methoxy-2-methylpropanamide
CAS Number:82473-56-1
Molecular formula:C5H11NO2
Molecular Weight:117.15

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Yield:82473-56-1 70%

Reaction Conditions:

Stage #1: 2-methyl-2-methoxypropanoic acidwith benzotriazol-1-ol;N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride in acetonitrile at 20; for 2 h;
Stage #2: with ammonium hydroxide in acetonitrile at 20;

Steps:

B1 Example B1

A solution of 2-methoxy-2-methylpropanoic acid (1.24 g, 10.50 mmol) and HOBt (2.090 g, 13.65 mmol) in MeCN (26.2 mL) was treated portion-wise with EDC (2.62 g, 13.65 mmol) and stirred at RT for 2 h. NH₄OH (?15 M, 2.04 mL, ?30.6 mmol) was added and the mixture was stirred at RT overnight.
The mixture was treated with 50% satd.
brine, saturated with solid NaHCO₃, extracted with EtOAc (3*) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford 2-methoxy-2-methylpropanamide (860 mg, 70%).
¹H NMR (400 MHz, DMSO-d₆): δ 7.14 (s, 1H), 7.02 (s, 1H), 3.12 (s, 3H), 1.21 (s, 6H).

References:

US2014/275016,2014,A1 Location in patent:Paragraph 0246