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

To a cold (ice bath) solution of 98.5 g (10 mole) of phosgene in 500 ml of methylene chloride was added dropwise a solution of 129.2 g (1.0 mole) 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 for 1 hr and then treated dropwise with 140 ml (101 g, 1.0 mole) of triethylamine at such a rate that the temperature did not exceed 25° C. The mixture was stirred at ambient temperature for 3 hr and then treated with 500 ml of 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 over sodium sulfate 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, b.p. 110° C. at 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 hr
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 over sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customto give a brown oil as residue
10. distillationThe oil was subjected to vacuum distillation

ORD record

ord-45612324b69e470a98bf9290c25118c2

Source dataset

uspto-grants-1989_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04886794