(R)(+)-ALPHA-PHENETHYLUREA synthesis
- Product Name:(R)(+)-ALPHA-PHENETHYLUREA
- CAS Number:16849-91-5
- Molecular formula:C9H12N2O
- Molecular Weight:164.2
Yield:16849-91-5 97%
Reaction Conditions:
with hydrogenchloride in water at 80; for 1 h;
Steps:
30 Preparation of (R)-1-(1-Phenylethyl)urea
Preparation of (R)-1-(1-Phenylethyl)urea: A mixture of (R)-l-phenylemylamine (1.00 g, 8.25 mmol) in water (4 mL) was treated with a 1 M solution of HCl in water (8.5 mL, 8.5 mmol) followed by potassium cyanate (3.35 g, 41.2 mmol). The reaction mixture was warmed to 80 °C for 1 hour and cooled. The mixture was neutralized with saturated NaHC03 and extracted with ethyl acetate and 2- methyltetrahydrofuran. The combined organic phase was dried (Na2S04), filtered and concentrated. Chromatography on Si02 (0- 10% MeOH/DCM) gave the desired urea product (1.32 g, 8.04 mmol; 97%) as a white solid. MS ESI calc'd for C9H12N20 [M + H]+ 165, found 165. 1H NMR (600 MHz, DMSO- /6) δ 7.23-7.28 (m, 4 H), 7.17 (t, J= 6.7 Hz, 1 H), 6.38 (d, J = 7.9 Hz, 1 H), 5.38 (br s, 2 H), 4.65 (m, 1 H), 1.26 (d, J= 7.1 Hz, 3 H).
References:
WO2013/63214,2013,A1 Location in patent:Page/Page column 111
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