Urea → 2-Methoxyaniline

5-(2-Methoxy-benzyl)-oxazol-2-ylamine A mixture of 2-chloro-3-(2-methoxylphenyl)-propionaldehyde (10 g, crude from above) and urea (9.6 g, 0.16 mol) was dissolved in ethanol (250 mL) and then heated at reflux overnight. The solvent was evaporated to dryness. The residue was diluted with dichloromethane (250 mL) and then washed with sodium hydroxide (10% aqueous solution, 100 mL) and water (50 mL). The organic layer was extracted three times with hydrochloric acid (5% aqueous solution, 250 mL). The combined aqueous layers were adjusted to pH 9 to 10 with a 10% aqueous solution of sodium hydroxide and then extracted three times with dichloromethane (300 mL). The organic layer was separated, dried over sodium sulfate, and evaporated to dryness. The crude product was purified by silica gel column chromatography to yield the yellow-red solid product (0.72 g, 0.35% from 2-methoxyaniline). ESI-MS m/z calc. 204.1, found 205.1 (M+1)+; 1H NMR (CDCl3) δ 7.26-7.20 (m, 1H), 7.14 (d, J=7.2 Hz, 1H), 6.91-6.86 (m, 2H), 6.35 (s, 1H), 4.49 (bs, 2H), 3.85 (s, 2H), 3.82 (s, 3H).

1. temperatureheated
2. temperatureat reflux overnight
3. customThe solvent was evaporated to dryness
4. additionThe residue was diluted with dichloromethane (250 mL)
5. washwashed with sodium hydroxide (10% aqueous solution, 100 mL) and water (50 mL)
6. extractionThe organic layer was extracted three times with hydrochloric acid (5% aqueous solution, 250 mL)
7. extractionextracted three times with dichloromethane (300 mL)
8. customThe organic layer was separated
9. dry with materialdried over sodium sulfate
10. customevaporated to dryness
11. customThe crude product was purified by silica gel column chromatography

ORD record

ord-c1741c3b5a2e4134a743c4035f5b06b8

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977322B2