Ammonium Hydroxide → 2-(4-Hydroxyphenyl)-1,3-thiazole-4-carboxamide

Temperature

0 °C

2-(4-Hydroxyphenyl)-1,3-thiazole-4-carboxylic acid (0.835 g, 3.77 mmol) was dissolved in 20 ml of dry tetrahydrofuran and cooled to 0° C. (Chloromethylene)dimethylammonium chloride (0.58 g, 4.53 mmol) was added in one portion. The mixture was stirred at 0° C. for 5 h. 28% Ammonium hydroxide aqueous solution (5 ml) was added, and the reaction mixture was stirred for 15 h at the room temperature. The organic solvent was removed in vacuo and the residue was partitioned between ethyl acetate and saturated sodium carbonate solution. The organic layer was separated and the aqueous phase was extracted twice with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (0 to 10% methanol in dichloromethane) to give the title compound as beige solid.

1. additionwas added in one portion
2. stirringthe reaction mixture was stirred for 15 h at the room temperature
3. customThe organic solvent was removed in vacuo
4. customthe residue was partitioned between ethyl acetate and saturated sodium carbonate solution
5. customThe organic layer was separated
6. extractionthe aqueous phase was extracted twice with ethyl acetate
7. washThe combined extracts were washed with brine
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated in vacuo
10. customThe residue was purified by silica gel column chromatography (0 to 10% methanol in dichloromethane)

ORD record

ord-bd795415b8ba4acf8eb567267fabc6db

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633175B2