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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1044725Generated: October 31, 2026

Thionyl Chloride → 5-(4-Chloroquinazolin-6-yl)furan-2-carbaldehyde

https://huagongshe.com/reaction/1044725

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThionyl ChlorideHCID 24386—
Reactant5-(4-Hydroxy-6-quinazolinyl)furan-2-carbaldehydeHCID 136162616—
CatalystDimethylformamideHCID 6228—
Product5-(4-Chloroquinazolin-6-yl)furan-2-carbaldehydeHCID 53390821—

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of the compound of formula (IX) (3 g, 12 5 mmol), SOCl2 (30 mL) and one drop of DMF was heated at 80° C. until the reaction was complete (TLC analysis). The volatile components were evaporated (including SOCl2) to provide crude compound of formula (Xa) that was purified by column chromatography (eluting with EtOAc/DCM, 1:8, v/v) to give free base of the compound of formula (Xa). The compound of formula (Xa) 1H NMR (300 MHz, d6-DMSO): δ 7.53 (d, J=3.3 Hz, 1H), 7.68 (d, J=3.3 Hz, 1H), 8.02 (d, J=8.7 Hz, 1H), 8.42 (d, J=8.4 Hz, 1H), 8.50 (s, 1H), 8.90 (s, 1H), 9.64 (s, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08563719B2
Source datasetuspto-grants-2013_10
ORD IDord-e3cc74854e784c3e97945009443553a5
Source noteuspto-grants-2013_10