Dimethyl Sulfoxide → 4-(Furan-2-yl)-N-(2-oxocyclohexyl)-1,3-thiazole-2-carboxamide

Temperature

-60 °C

Oxalyl chloride (0.776 mL, 1.55 mol) and dimethyl sulfoxide (0.240 mL, 3.38 mmol) were dissolved in dichloromethane (3 mL), and the mixture was stirred at −60° C. for 10 minutes. To the solution was added 4-(2-furyl)-N-(2-hydroxycyclohexyl)thiazole-2-carboxamide (413 mg, 1.41 mmol) obtained in Step 1 and the mixture was stirred for 15 minutes. Triethylamine (0.983 mL, 7.05 mmol) was added to the mixture, and the mixture was stirred at room temperature for 10 minutes, then water and ethyl acetate were added thereto and the mixture was extracted. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give 4-(2-furyl)-N-(2-oxocyclohexyl)thiazole-2-carboxamide (339 mg, 83%).

1. stirringthe mixture was stirred for 15 minutes
2. stirringthe mixture was stirred at room temperature for 10 minutes
3. extractionthe mixture was extracted
4. washThe organic layer was washed with brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was then evaporated under reduced pressure
7. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

ORD record

ord-49a867885bce44ba88bd17531c4b521f

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928098B2