2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 24967085, compound

HRID 545631Notes

Reaction equation

[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[CH2:11][NH:10][C:9]1=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[CH:11]=[N:10][C:9]1=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring solution of 1-benzyl-6-chloro-3,4-dihydroquinazolin-2(1H)-one (0.15 g, 0.55 mmol) in DCM (5 mL) was added DDQ (0.13 g, 0.55 mmol) at 0° C. upon which the solution turned black. The mixture was stirred for 4 h at 0° C. and quenched with 1N NaOH(aq). The mixture was passed through a short path of Celite. The separated aqueous layer was extracted with DCM (2×15 mL) and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a crude residue, which was purified using flash column chromatography (100% DCM to 4% MeOH in DCM gradient). The product fractions were concentrated, and washed with ether-hexanes and iPrOH successively to obtain the title compound 1-Benzyl-6-chloroquinazolin-2(1H)-one as an off-white solid. MS m/e 271 (M+H)+.

Workup

customquenched with 1N NaOH(aq)
extractionThe separated aqueous layer was extracted with DCM (2×15 mL)
washthe combined organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customto give a crude residue, which
customwas purified
concentrationThe product fractions were concentrated
washwashed with ether-hexanes and iPrOH successively

Sources & evidence

ORD record: ord-6a2b9ead17bf47b78ed2b17af637d8b2
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935709B2

Reaction notes

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