Hydrochloric Acid → HCID 21180334, Verbindung

To a solution of 4-(difluoromethoxy)benzonitrile (5 g, 30 mmol) in ethanol at 4° C. was bubbled dry HCl(g) for 3 h. The resulting mixture was stoppered and kept at 4° C. for 65 h. Ether (40 ml) was then added with ultrasonication to precipitate the imidate hydrochloride salt, which was washed twice with dry ether (40 ml) and then dried under vacuum (0.05 mmHg) at 20° C. To a solution of imidate hydrochloride salt (1 g, 4 mmol) in ethanol (15 ml) was added sodium ethoxide solution dropwise (sodium: 98 mg, 4 mmol in 5 ml of dry ethanol) at room temperature. The reaction was allowed to stir for a further 30 min then 3-[1,3]Dioxolan-2-yl-benzoic acid hydrazide was added (824 mg, 4 mmol) and the mixture was heated to reflux for 22 h until the starting materials were consumed. The reaction mixture was evaporated to dryness and chromatographed over SiO2 (Merck 230-400 mesh) eluting with EtOAc/nHexane (3:7), the product fractions were combined and evaporated to afford the title compound as a white solid (885 mg, 62% yield), MS: m/e=359.1 (M+).

1. customto precipitate the imidate hydrochloride salt, which
2. washwas washed twice with dry ether (40 ml)
3. customdried under vacuum (0.05 mmHg) at 20° C
4. temperaturethe mixture was heated
5. temperatureto reflux for 22 h until the starting materials
6. customwere consumed
7. customThe reaction mixture was evaporated to dryness
8. customchromatographed over SiO2 (Merck 230-400 mesh)
9. washeluting with EtOAc/nHexane (3:7)
10. customevaporated

ORD-Eintrag

ord-136f5332684a4bc5a812e485ebc51524

Quelldatensatz

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06265426B1