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

HRID 1044725Notes

Reaction equation

O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[O:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=3)[CH:10]=2)[N:5]=[CH:4][NH:3]1.O=S(Cl)[Cl:21]>CN(C=O)C>[Cl:21][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[O:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=3)[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

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).

Workup

customThe volatile components were evaporated (including SOCl2)
customto provide crude compound of formula (Xa) that
customwas purified by column chromatography (eluting with EtOAc/DCM, 1:8, v/v)
customto give free base of the compound of formula (Xa)

Sources & evidence

ORD record: ord-e3cc74854e784c3e97945009443553a5
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563719B2

Reaction notes

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