Hydrochloric Acid → 5-(4-Chloroquinazolin-6-yl)furan-2-carbaldehyde hydrochloride

HRID 1044718Notes

Reaction equation

O=S(Cl)[Cl:3].O=[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[O:20][C:19]([CH:21]=[O:22])=[CH:18][CH:17]=3)[CH:14]=2)[N:9]=[CH:8][NH:7]1.CN(C=O)C.[ClH:28]>CC#N>[ClH:3].[Cl:28][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[O:20][C:19]([CH:21]=[O:22])=[CH:18][CH:17]=3)[CH:14]=2)[N:9]=[CH:8][N:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Over a 1.5 hour period under an atmosphere of N2, SOCl2 (86.2 g) in MeCN (145 mL) was added dropwise into a mixture, that had been preheated at reflux for 0.5 h, of the compound of formula (IX) (29 g, 0.121 mol), MeCN (435 mL) and DMF (0.88 g) at reflux. The reaction was terminated when less than 2% (HPLC) of the compound of formula (IX) was remaining. If the reaction did not achieve complete reaction, extra SOCl2 was added. The mixture was cooled to about 25±5° C. (internal temperature), and was then filtered and washed with MeCN (58 mL) to give ca. 55 g of (Xa).HCl (moist with MeCN) with 82A % purity by HPLC. (Xa).HCl: 1H NMR (300 MHz, d6-DMSO): δ 9.68 (s, 1H), 9.17 (s, 1H), 8.57 (d, J=2.0 Hz, 1H), 8.46 (dd, J=8.6, 2.1 Hz, 1H), 8.02 (d, J=8.6 Hz, 1H), 7.74 (d, J=3.8 Hz, 1H), 7.60 (d, J=3.8 Hz, 1H). See FIG. 5 for the 1H NMR spectrum of (Xa).HCl; 13C NMR (75 MHz, d6-DMSO) δ 179.0, 159.6, 156.4, 152.9, 149.5, 141.0, 132.6, 129.2, 125.9, 123.2, 122.9, 122.7, 111.5.

Workup

temperatureat reflux
customThe reaction was terminated when less than 2% (HPLC) of the compound of formula (IX)
customreaction, extra SOCl2
additionwas added
filtrationwas then filtered
washwashed with MeCN (58 mL)
customto give ca. 55 g of (Xa)

Sources & evidence

ORD record: ord-5ffe245087bb438babf88e627bd89f23
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563719B2

Reaction notes

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