Hydrochloric Acid → HCID 18470248, compound

Temperature

-70 °C

To a solution of 2-methyl-2-thiazoline (1.01 g) in dry tetrahydrofuran at −70° C. was added a solution of n-butyl lithium in hexanes (2.5M, 4.0 ml) dropwise over 10 min. After stirring at −70° C. for 2 h, 1,7-dibromoheptane (12.9 g) was added in one portion (temperature increased to −45° C.). The mixture was cooled again to −70° C. for 1 h and then allowed to warm to room temperature over 1 h. The mixture was cooled to 0° C. and water (10 ml) added, followed by dilute hydrochloric acid (to pH 2). The organic layer was separated and the aqueous layer extracted with diethyl ethyl (2×20 ml). The organic layers were combined and washed with water and brine and dried over magnesium sulfate. Evaporation under reduced pressure gave an oil that was chromatographed on silica gel using 40-60° C. petroleum ether:ethyl acetate 5:1 to give 1-bromo-8-(2-thiazolinyl)octane (1.06 g). 1H-NMR (CDCl3) δ 1.2-1.5 (6H, m), 1.5-1.75 (4H, m), 1.75-1.95 (2H, m), 2.50 (2H, t), 3.28 (2H, t), 3.40 (2H, t) and 4.21 (2H, dt).

1. temperatureThe mixture was cooled again to −70° C. for 1 h
2. temperatureto warm to room temperature over 1 h
3. temperatureThe mixture was cooled to 0° C.
4. customThe organic layer was separated
5. extractionthe aqueous layer extracted with diethyl ethyl (2×20 ml)
6. washwashed with water and brine
7. dry with materialdried over magnesium sulfate
8. customEvaporation under reduced pressure
9. customgave an oil that
10. customwas chromatographed on silica gel using 40-60° C. petroleum ether:ethyl acetate 5:1

ORD record

ord-67eb798d35cb43848934754cce302a9e

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06417192B1