Hydrogen Peroxide → HCID 90418865, compound

Temperature

25 °C

Into a 100-mL round-bottom flask, was placed a solution of 3-chloro-5-(4-methoxyphenyl)-1,2-thiazole-4-carbonitrile (3.4 g, 13.56 mmol, 1.00 equiv) in ethanol/H2O (20/10 mL), sodium hydroxide (1 g, 25.00 mmol, 1.84 equiv), H2O2 (10 g). The resulting solution was stirred overnight at 25° C. The resulting mixture was concentrated under vacuum. The reaction was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×80 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 (1:2). This resulted in 680 mg (crude) of 3-chloro-5-(4-methoxyphenyl)-1,2-thiazole-4-carboxamide as a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C11H9ClN2O2S, 269.0 (M+H). found 269.0.

1. customInto a 100-mL round-bottom flask, was placed
2. concentrationThe resulting mixture was concentrated under vacuum
3. customThe reaction was then quenched by the addition of 50 mL of water
4. extractionThe resulting solution was extracted with 3×80 mL of ethyl acetate
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationThe solids were filtered out
7. concentrationThe resulting mixture was concentrated under vacuum
8. customThis resulted in 680 mg (crude) of 3-chloro-5-(4-methoxyphenyl)-1,2-thiazole-4-carboxamide as a yellow solid

ORD record

ord-f69af62b2eb94913a77d9498eb487399

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1