Hydrochloric Acid → HCID 21847063, compound

Temperature

80 °C

2-Chloro-5-chloromethylthiazole hydrochloride (100 g, 0.49 mole), and water (100 mL) were charged to a flask. The mixture was stirred and heated to 80° C. for 2.5 hours. The reaction mixture was cooled to about 15° C. and sodium carbonate (51.5 g) was added (to raise the pH to about 8-9). The product was extracted with ethyl acetate (1×500 mL and 1×250 mL). The combined organic extracts were stirred for 20 minutes with 3 g of decolorizing carbon (Norit® SA3 about 100 mesh) and filtered through celite. The celite and flask were washed with an additional 100 mL of ethyl acetate and combined with the filtrate. The filtrate was concentrated under reduced pressure to provide a yellow-orange oil. The oil was dissolved in 500 mL of ethyl acetate and cooled to -10° C., under a nitrogen atmosphere. A solution of HCl (17.82 grams, 1 eq.) in ethyl acetate was slowly added. The temperature was maintained below -5° C. After the addition was complete the slurry formed was stirred for 30 minutes. The product was filtered under vacuum and the flask and product washed with ethyl acetate(100 mL). The title compound, an off white powder, was purged with nitrogen gas until dry. Yield 63.3 g; 69.6%..

1. temperatureThe reaction mixture was cooled to about 15° C.
2. temperatureto raise the pH to about 8-9)
3. extractionThe product was extracted with ethyl acetate (1×500 mL and 1×250 mL)
4. stirringThe combined organic extracts were stirred for 20 minutes with 3 g of decolorizing carbon (Norit® SA3 about 100 mesh)
5. filtrationfiltered through celite
6. washThe celite and flask were washed with an additional 100 mL of ethyl acetate
7. concentrationThe filtrate was concentrated under reduced pressure
8. customto provide a yellow-orange oil
9. temperaturecooled to -10° C., under a nitrogen atmosphere
10. temperatureThe temperature was maintained below -5° C
11. additionAfter the addition
12. customformed
13. stirringwas stirred for 30 minutes
14. filtrationThe product was filtered under vacuum
15. washthe flask and product washed with ethyl acetate(100 mL)
16. customThe title compound, an off white powder, was purged with nitrogen gas
17. customuntil dry

ORD record

ord-2a1174ad73ad493e890f33954db96f0b

Source dataset

uspto-grants-1999_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05959118