2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 135754581, compound

HRID 2211946Notes

Reaction equation

HRID 2211946 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([CH2:19][OH:20])=[CH:14][CH:13]=3)=[N:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([CH:19]=[O:20])=[CH:14][CH:13]=3)=[N:2]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 135754608HCID 135754608, compound

Product 1

HCID 135754581HCID 135754581, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the alcohol (6-2, 29 mg, 0.11 mmol) in tetrahydrofuran (2 mL) was added at the ambient temperature 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (75 mg, 0.33 mmol). After 5 h stirring, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, separated, dried (MgSO4) and concentrated in vacuo. Chromatography (SiO2, 50% ethyl acetate in hexanes) afforded the desired product (6-3) as a light tan solid; 1H NMR (400 MHz, DMSO-d6) δ 13.42 (s, 1H), 11.14 (s, 1H), 9.98 (s, 1H), 8.22 (d, 1H, J=8.4 Hz), 8.20 (s, 1H), 7.70–7.56 (m, 3H), 7.46 (t, 1H, J=7.8 Hz), 7.36 (s, 1H), 7.28 (t, 1H, J=7.8 Hz).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. customseparated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-67698cfffcae4641a1289f49f54dfbb2
Source dataset
uspto-grants-2006_09
Patent number
US07101884B2

Reaction notes

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