Methyl propiolate → Methyl 2-methyl-1H-imidazole-5-carboxylate

A solution of N′-hydroxyethanimidamide (65 g, 880 mmol) in anhydrous methanol (2 L) was treated with methyl propiolate (100 g, 1.19 mol), and the reaction was heated at reflux for 4 hours. The reaction mixture was concentrated in vacuo, and the residue was diluted with diphenyl ether (1 L) and heated at reflux for 4 hours. The hot solution was filtered, and the filtrate was cooled to room temperature and diluted with hexanes (2 L). The resulting solid was washed with diethyl ether (1 L), to afford the product as a brown solid. Yield: 60 g, 430 mmol, 49%.

1. temperaturethe reaction was heated
2. temperatureat reflux for 4 hours
3. concentrationThe reaction mixture was concentrated in vacuo
4. additionthe residue was diluted with diphenyl ether (1 L)
5. temperatureheated
6. temperatureat reflux for 4 hours
7. filtrationThe hot solution was filtered
8. additiondiluted with hexanes (2 L)
9. washThe resulting solid was washed with diethyl ether (1 L)

ORD 기록

ord-e16061c9c0d340a596addc0648099cde

출처 데이터셋

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09296761B2