2-Chloroethyl isocyanate → HCID 49855325, compound

Commercially available 2-chloroethylisocyanate (3.10 mL, 36.45 mmol) was added slowly to a solution of 2-methoxybenzylamine (5.00 mL, 36.45 mmol) in dichloromethane (60 mL) at room temperature. The resulting reaction mixture was stirred for 30 minutes and the intermediate product thus formed was filtered and washed with hexane, and then suspended in water (150 mL). This suspension was heated to reflux and stirred at refluxing for 2 hours, then cooled to room temperature. The reaction mixture was extracted with ethyl acetate, and the aqueous phase was basified with ammonium hydroxide to pH=14. The basified aqueous phase was then extracted with ethyl ether (50 mL) 3 times and the combined organic phases were dried with magnesium sulfate. Concentration gave 5.10 g of N-(2-methoxybenzyl)-4,5-dihydrooxazol-2-amine. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ=3.80 (t, 2H, J=10.1 Hz), 3.85 (s, 3H), 4.26 (t, 2H, J=10.1 Hz), 4.38 (s, 2H), 6.83-6.95 (m, 2H), 7.20-7.32 (m, 2H).

1. customThe resulting reaction mixture
2. customthe intermediate product thus formed
3. filtrationwas filtered
4. washwashed with hexane
5. temperatureThis suspension was heated
6. temperatureto reflux
7. stirringstirred
8. temperatureat refluxing for 2 hours
9. extractionThe reaction mixture was extracted with ethyl acetate
10. extractionThe basified aqueous phase was then extracted with ethyl ether (50 mL) 3 times
11. dry with materialthe combined organic phases were dried with magnesium sulfate
12. concentrationConcentration

ORD record

ord-9a75ca0ae23b4dbda2b9cf0b434ebc65

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329918B2