o-Chloranil → HCID 10977652, compound

HRID 218230

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-e05c045a5d854c5fa0fc5fce0d3dc51b
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198331B2

Linked notes

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