1,3-Dichloro-2-propanol → 5-(Chloromethyl)-3-methyl-2-oxazolidinone

A solution of 64.5 g (0.5 mol) of 1,3-dichloro-2-propanol (Eastman, practical) in 200 mL of methylene chloride was treated with 28.5 g (0.5 mol) of methyl isocyanate and a few drops of triethylamine and allowed to stir at ambient temperature overnight. The solution was concentrated and the residue was dissolved in 200 mL of 95% ethanol and treated with a solution of 33.6 g (0.6 mol) of potassium hydroxide in 300 mL of 95% ethanol. The mixture was stirred at ambient temperature for 3.5 h and then concentrated. The residue was partitioned between 250 mL of benzene and 100 mL of water. The organic layer was washed successively with 50 mL of a 2N hydrochloric acid solution and 100 mL brine, dried (Na2SO4) and concentrated to give 50.5 g of oil which was subjected to vacuum distillation to yield 36.9 g (49%) of clear oil, bp 131°-133° C. (0.3 mm).

1. concentrationThe solution was concentrated
2. dissolutionthe residue was dissolved in 200 mL of 95% ethanol
3. stirringThe mixture was stirred at ambient temperature for 3.5 h
4. concentrationconcentrated
5. customThe residue was partitioned between 250 mL of benzene and 100 mL of water
6. washThe organic layer was washed successively with 50 mL of a 2N hydrochloric acid solution and 100 mL brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated

ORD record

ord-e370e8034c9846fa85ef0ab70f0c34b8

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05086055