1,1-Dimethoxyethyl(dimethyl)amine → 3-(3-Methyl-1,2,4-oxadiazol-5-yl)benzaldehyde

Temperature

90 °C

A mixture of 3-[1,3]dioxolan-2-yl-benzamide (2.3 g) and dimethylacetamide dimethylacetal (4 g) was heated under reflux for 1 hour and then evaporated to dryness. The oily residue was dissolved in dioxane (20 mL) and hydroxylamine hydrochloride (1.18 g), acetic acid (20 mL) and a 2N aqueous sodium hydroxide solution (9 mL) were added and the mixture was heated at 90° C. for 2 hours. After evaporation, the residue was dissolved in toluene (100 mL) and a 1N hydrochloric acid solution (50 mL) was added and the mixture was stirred at reflux for 2 hours. After cooling at room temperature the organic phase was decanted, washed with water, dried over Na2SO4, filtered and evaporated to give the title compound (2.3 g) as a white solid.

1. temperaturewas heated
2. temperatureunder reflux for 1 hour
3. customevaporated to dryness
4. dissolutionThe oily residue was dissolved in dioxane (20 mL)
5. additionhydroxylamine hydrochloride (1.18 g), acetic acid (20 mL) and a 2N aqueous sodium hydroxide solution (9 mL) were added
6. customAfter evaporation
7. dissolutionthe residue was dissolved in toluene (100 mL)
8. additiona 1N hydrochloric acid solution (50 mL) was added
9. temperatureat reflux for 2 hours
10. temperatureAfter cooling at room temperature the organic phase
11. customwas decanted
12. washwashed with water
13. dry with materialdried over Na2SO4
14. filtrationfiltered
15. customevaporated

ORD record

ord-627812b91be54b5c8e9f2a7ad0539939

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06552022B1