Diethyl Sulfate → Ethyl 3,5-dichloro-1,2-thiazole-4-carboxylate

Temperature

0 °C

Into a 500-mL round-bottom flask, was placed dichloro-1,2-thiazole-4-carboxylic acid (10 g, 50.50 mmol, 1.00 equiv), acetone (100 mL). This was followed by the addition of EtOSO3Et (19.54 g) dropwise with stirring at 0° C. in 3 min. To this was added potassium carbonate (28.02 g, 202.73 mmol, 4.01 equiv). The resulting solution was stirred for 30 min at 58° C. in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 100 mL of H2O. The resulting solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (12:88). This resulted in 1.353 g (12%) of ethyl 3,5-dichloro-1,2-thiazole-4-carboxylate as yellow oil.

1. customInto a 500-mL round-bottom flask, was placed
2. stirringThe resulting solution was stirred for 30 min at 58° C. in an oil bath
3. concentrationThe resulting mixture was concentrated under vacuum
4. additionThe resulting solution was diluted with 100 mL of H2O
5. extractionThe resulting solution was extracted with 3×100 mL of ethyl acetate
6. dry with materialdried over anhydrous sodium sulfate
7. customThis resulted in 1.353 g (12%) of ethyl 3,5-dichloro-1,2-thiazole-4-carboxylate as yellow oil

ORD record

ord-10fc93d6db374853bd2f1ec25bda398c

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1