CarbaMic acid, N-(2,2-diMethoxyethyl)-N-2-propen-1-yl-, phenylMethyl ester synthesis
- Product Name:CarbaMic acid, N-(2,2-diMethoxyethyl)-N-2-propen-1-yl-, phenylMethyl ester
- CAS Number:569682-60-6
- Molecular formula:C15H21NO4
- Molecular Weight:279.33
114790-39-5
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Yield:569682-60-6 98%
Reaction Conditions:
with potassium hydroxide;N-benzyl-N,N,N-triethylammonium chloride in toluene at 50; for 48 h;Inert atmosphere;
Steps:
18.B
To a 500 ml_ round-bottomed flask equipped with thermocouple probe, nitrogen inlet, reflux condenser, heating mantle, and mechanical stirring was added (2,2- dimethoxy-ethyl)-carbamic acid benzyl ester (50 g, 209 mmol) in toluene (180 ml_). To the resulting solution was added powdered KOH (51 .6 g, 920 mmol) and triethylbenzylammonium chloride (0.810 g, 3.55 mmol). A solution of allyl bromide (33.0 g, 275 mmol) in toluene (50 ml_) was added dropwise over 10 minutes. The mixture was heated to 50 °C and stirred for 2 days. To the reaction mixture was added water (230 ml_) over ten minutes. The layers were separated and the aqueous was extracted with toluene (2 x 200 ml_). The combined organics were washed with brine (1 x 200 ml_), dried withmagnesium sulfate, filtered, and concentrated to afford the title compound (57.8 g, 98%). 1 H-NMR (CDCI3, 500 MHz): 7.31 (m, 5H), 5.76 (m, 1 H), 5.15 (m, 4H), 4.51 (m, 1 H), 3.98 (d, J=9.48, 2H), 3.36 (m, 8H).
References:
WO2011/50200,2011,A1 Location in patent:Page/Page column 57-58
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