Aminoacetaldehyde dimethyl acetal → 2-(4-NITRO-BENZYL)-1H-IMIDAZOLE

Temperature

60 °C

To a solution of ethyl 2-(4-nitrophenyl)-acetimidate hydrochloride (3.5 g, 14.3 mmol) in ethanol (15 mL) was added amino acetaldehyde dimethyl acetal (1.87 mL, 17.2 mmol) and the reaction heated at reflux for 18 h. The reaction mixture was concentrated which was mixed with 2N hydrochloric acid (30 mL) and heated to 60° C. for 18 h. The solvent was evaporated, diluted with water and extracted with ethyl acetate. The organic layer was separated, the aqueous layer basified with sodium carbonate and extracted with chloroform (×2). The combined chloroform extracts was dried over sodium sulfate, filtered and evaporated under reduced pressure to obtain 2-(4-nitro-benzyl)-1H-imidazole (1.5 g, 51%) as a brown solid.

1. temperaturethe reaction heated
2. temperatureat reflux for 18 h
3. concentrationThe reaction mixture was concentrated which
4. additionwas mixed with 2N hydrochloric acid (30 mL)
5. customThe solvent was evaporated
6. additiondiluted with water
7. extractionextracted with ethyl acetate
8. customThe organic layer was separated
9. extractionextracted with chloroform (×2)
10. dry with materialThe combined chloroform extracts was dried over sodium sulfate
11. filtrationfiltered
12. customevaporated under reduced pressure

ORD record

ord-7fd81ecaea744fad8fd06a73f2da3724

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604029B2