Hydrochloric Acid → 3-(4-Bromobutyl)-2,5,5-trimethyl-4-thiazolidinone

Temperature

-40 °C

To a -73° C. solution of 3-(4-bromobutyl)-2-methyl-4-thiazolidinone (6.00 g), methyliodide (10.99 g) and THF (50 ml) under nitrogen was added lithium bis(trimethylsilyl)amide (0.0500 mol) in THF (50 ml) at a rate to maintain the internal temperature below -55° C. The resulting solution was stirred at <-55° C. for 10 minutes, allowed to warm to -40° C., and at which temperature 1N HCl (250 ml) was added. The aqueous mixture was extracted with 25% benzene/ether (3×125 ml). The combined extracts were washed with brine (200 ml), dried (Na2SO4), and concentrated to a liquid which was chromatographed on silica gel yielding 5.07 g of a liquid. The liquid was distilled to give 3.80 g of a clear liquid, b.p. 109°-114° C. at 0.20 mmHg.

1. temperatureto maintain the internal temperature below -55° C
2. extractionThe aqueous mixture was extracted with 25% benzene/ether (3×125 ml)
3. washThe combined extracts were washed with brine (200 ml)
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated to a liquid which
6. customwas chromatographed on silica gel yielding 5.07 g of a liquid
7. distillationThe liquid was distilled

ORD record

ord-42dc79853bac44729c463f115f40bb1b

Source dataset

uspto-grants-1993_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05229388