Hydrochloric Acid → HCID 22482776, compound

Temperature

-15 °C

152.2 g (0.594 mol, 1.10 eq) of butyllithium solution (25% strength in heptane) were added dropwise under nitrogen in the course of 30 min to a solution of 90.8 ml (65.6 g, 0.648 mol, 1.20 eq) of diisopropylamine in 800 ml of absolute MTBE at −15° C. This solution was stirred at −15° C. for 30 min. 400 ml of the MTBE solution containing the 4-carbethoxy-2-phenyl-thiazoline were added dropwise at −15° C. in the course of 30 min and the mixture was stirred at −15° C. for 1 h, whereby a brown solution resulted. 115.0 g (50.4 ml, 0.81 mol, 1.50 eq) of methyl iodide were added and the reaction mixture was warmed to 23° C. and stirred at this temperature for a further 3 h. 300 ml of 2 M HCl were then slowly added with vigorous stirring, then the mixture was adjusted to pH 2-3 so that the temperature did not exceed 30° C. The two-phase mixture obtained thereby was stirred for a further 30 min. The organic phase was then separated off. This MTBE solution, containing 4-carbethoxy-4-methyl-2-phenylthiazoline, was employed in stage 3.

1. additionwere added dropwise at −15° C. in the course of 30 min
2. stirringthe mixture was stirred at −15° C. for 1 h
3. customwhereby a brown solution resulted
4. temperaturethe reaction mixture was warmed to 23° C.
5. stirringstirred at this temperature for a further 3 h
6. customdid not exceed 30° C
7. customThe two-phase mixture obtained
8. stirringthereby was stirred for a further 30 min
9. customThe organic phase was then separated off
10. additionThis MTBE solution, containing 4-carbethoxy-4-methyl-2-phenylthiazoline

ORD record

ord-b5d8923654464bb5a57ef5db08531f74

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06894170B2