2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 69752497, compound

HRID 585900Notes

Reaction equation

[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:36])[NH:17][C:18]([N:21]3[C:29]4[C:28]5[CH:30]=[CH:31][C:32]([O:34][CH3:35])=[CH:33][C:27]=5[CH2:26][CH2:25][C:24]=4[CH:23]=[N:22]3)([CH3:20])[CH3:19])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.C([O-])(O)=O.[Na+]>O1CCOCC1>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16](=[O:36])[NH:17][C:18]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]5[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:28]5=4)[CH:23]=[N:22]3)([CH3:20])[CH3:19])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of the product from Step B (0.11 g, 0.23 mmol) in 1,4-dioxane (10 mL) was added DDQ (0.19 g, 0.8 mmol) and the solution stirred at 23° C. for 72 h. The solution was poured into aqueous NaHCO3 and the mixture was extracted with ethyl acetate (2×20 mL). The combined organic extracts were dried (MgSO4) and concentrated to a residue, which was purified by chromatography (silica, 25% ethyl acetate in hexanes) to give an oil (0.1 g, 91%): 1H NMR (CDCl3) δ 8.5 (bs, 1H), 8.01 (s, 1H), 7.75 (d, J=6 Hz, 2H), 7.63 (d, J=12 Hz, 1H), 7.5 (bs, 1H), 7.4 (m, 3H), 7.3-7.2 (m, 5H), 5.2 (m, 1H), 5.0 (m, 1H), 4.75 (m, 1H), 4.4-4.3 (m, 2H), 4.1 (m, 1H), 3.93 (s, 3H), 1.21 (t, J=6 Hz, 3H); MS m/z 478 [M+H]+.

Workup

extractionthe mixture was extracted with ethyl acetate (2×20 mL)
dry with materialThe combined organic extracts were dried (MgSO4)
concentrationconcentrated to a residue, which
customwas purified by chromatography (silica, 25% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-c843cef131ee4e46832a6229d680793f
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06933392B2

Reaction notes

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