o-Chloranil → Diethyl 2-(thiazol-2(3H)-ylidene)malonate

HRID 491050Notes

Reaction equation

C(OC([N:6]1[CH:10]=[CH:9][S:8][CH:7]1[CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=O)C.ClC1C(=O)C(=O)C(Cl)=C(Cl)C=1Cl>ClCCl>[S:8]1[CH:9]=[CH:10][NH:6][C:7]1=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the product of Example 44A (12.9 g, 40.7 mmoles) in dichloromethane (100.0 ml) was added tetrachloro-1,2-benzoquinone (10.0 g, 40.7 mmoles) in portions at about 0° C., such that the mixture always had time to decolorize to a yellow-orange color. The mixture was then stirred for about 1 hour at 0° C. and was then washed with saturated aqueous sodium bicarbonate solution (200.0 ml) and brine (100.0 ml). The organic layer was dried over MgSO4, filtered, concentrated in vacuum and the crude product was purified by flash column chromatography on silica gel using hexanes/ethyl acetate (2:1) as the mobile phase to provide the title compound.

Workup

washwas then washed with saturated aqueous sodium bicarbonate solution (200.0 ml) and brine (100.0 ml)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuum
customthe crude product was purified by flash column chromatography on silica gel

Sources & evidence

ORD record: ord-960b55c652224fc8937b0e74251c1c80
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528282B2

Reaction notes

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