Methanol → Methyl 3,5-dichloro-1,2-thiazole-4-carboxylate

Into a 50-mL round-bottom flask, was placed dichloro-1,2-thiazole-4-carboxylic acid (400 mg, 2.02 mmol, 1.00 equiv), methanol (10 mL), sulfuric acid (2 mL). The resulting solution was heated to reflux overnight. The resulting mixture was concentrated under vacuum. The resulting solution was extracted with 3×20 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (5:100). This resulted in 350 mg (82%) of methyl 3,5-dichloro-1,2-thiazole-4-carboxylate as yellow oil.

1. customInto a 50-mL round-bottom flask, was placed
2. temperatureThe resulting solution was heated
3. temperatureto reflux overnight
4. concentrationThe resulting mixture was concentrated under vacuum
5. extractionThe resulting solution was extracted with 3×20 mL of ethyl acetate
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationThe solids were filtered out
8. concentrationThe resulting mixture was concentrated under vacuum
9. customThis resulted in 350 mg (82%) of methyl 3,5-dichloro-1,2-thiazole-4-carboxylate as yellow oil

ORD record

ord-c5ac08a31d1a4c8099b94e21dec6e7b7

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1