Hydrochloric Acid → 5-(2-Chloroethyl)-3-(1-methylethyl)-2-oxazolidinone

To a cold (ice bath) solution of 98.5 g (1.0 mol) of phosgene in 500 mL of methylene chloride was added dropwise a solution of 129.2 g (1.0 mol) of 1-isopropyl-3-pyrrolidinol in 250 mL of methylene chloride at such a rate that the temperature did not exceed 10° C. After addition was complete, the mixture was stirred in the cold bath for 1 h and then treated dropwise with 140 mL (101 g, 1.0 mol) of triethylamine at such a rate that the temperature did not exceed 25° C. The mixture was stirred at ambient temperature for 3 h and then treated with 500 mL of a 1N hydrochloric acid solution. The layers were separated and the organic layer was washed successively with 500 mL of a 1N hydrochloric acid solution, 500 mL of a 4% sodium hydroxide solution and 500 mL of brine, dried (Na2SO4) and concentrated under reduced pressure to give a brown oil as residue. The oil was subjected to vacuum distillation to yield 134.9 g (70%) of yellow oil, bp 119° C.@ 0.2 mm.

1. customdid not exceed 10° C
2. additionAfter addition
3. customdid not exceed 25° C
4. stirringThe mixture was stirred at ambient temperature for 3 h
5. customThe layers were separated
6. washthe organic layer was washed successively with 500 mL of a 1N hydrochloric acid solution, 500 mL of a 4% sodium hydroxide solution and 500 mL of brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under reduced pressure
9. customto give a brown oil as residue
10. distillationThe oil was subjected to vacuum distillation

ORD record

ord-c41f2e8962744888a02f950df371465d

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05086055