2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 178468702, compound

HRID 1526501Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a 250-mL round-bottom flask was placed a solution of ethyl 4-hydroxy-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine-6-carboxylate (4.0 g, 14.39 mmol, 1.00 equiv) in 1,4-dioxane (50 mL) was added DDQ (8 g, 35.24 mmol, 2.45 equiv) at room temperature. The resulting solution was stirred for 3 h at 90° C. under nitrogen. After cooling, the reaction was quenched with saturated aqueous Na2CO3. The solids were filtered out and the filtration was extracted with 3×100 mL of dichloromethane. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1) to give the resulted ethyl 3-hydroxy-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5,10,12-hexaene-12-carboxylate (2.2 g, 56%) as a brown solid.

Workup

customTo a 250-mL round-bottom flask was placed
temperatureAfter cooling
customthe reaction was quenched with saturated aqueous Na2CO3
filtrationThe solids were filtered out
filtrationthe filtration
extractionwas extracted with 3×100 mL of dichloromethane
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-5f578f64f16c42d9bc48b13ee466f7ad
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085586B2

Reaction notes

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