2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 178470648, compound

HRID 1526490Notes

Reaction equation

[OH:1][C:2]1[C:3]2[C:4]3[CH2:5][CH:6]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:7][CH2:8][C:9]=3[S:10][C:11]=2[N:12]=[CH:13][N:14]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[OH:1][C:2]1[C:3]2[C:4]3[CH:5]=[C:6]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:7]=[CH:8][C:9]=3[S:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of ethyl 2-[3-hydroxy-8-thia-4,6-diazatricyclo[7.4.0.0^[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]acetate (3.00 g, 10.26 mmol, 1.00 equiv) and DDQ (5.83 g, 25.68 mmol, 2.50 equiv) in 1,4-dioxane (30 mL) was stirred for 2 h at 90° C. in an oil bath under nitrogen. The reaction mixture was cooled to room temperature and quenched with saturated aqueous Na2CO3, extracted with 3×40 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:1) to provide the desired ethyl 2-[3-hydroxy-8-thia-4,6-diazatricyclo[7.4.0.0^[2,7]]trideca-1(9),2(7),3,5,10,12-hexaen-12-yl]acetate (2.00 g, 68%) as a yellow solid. LCMS (ES, m/z): 289 (M+H+).

Workup

temperatureThe reaction mixture was cooled to room temperature
customquenched with saturated aqueous Na2CO3
extractionextracted with 3×40 mL of ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum
customThe residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:1)

Sources & evidence

ORD record: ord-d888ae674afe4091bfcf2262e6543b52
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085586B2

Reaction notes

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