2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 57901913, compound

HRID 1928556Notes

Reaction equation

HRID 1928556 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[F:15][C:16]([F:42])([F:41])[S:17]([O:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]=1[CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33][NH:32]1)(=[O:19])=[O:18]>C(Cl)Cl>[F:42][C:16]([F:15])([F:41])[S:17]([O:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]=1[C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33][N:32]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 57901911HCID 57901911, compound

Product 1

HCID 57901913HCID 57901913, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Powdered 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) (46 mg, 0.2 mmol) was added to a solution of 2 (82 mg, 0.2 mmol) in CH2Cl2 (2 mL) at rt. After 20 minutes, the mixture was filtered through a short pad of silica gel using CH2Cl2 as the eluant. The solvent was evaporated and the residue was purified by column chromatography on silica gel (5:1 hexanes/EtOAc). The fractions containing the product (Rf=0.4) were collected and concentrated to yield the title product 3 (70 mg, 87% yield) as an oil. 1H NMR (CDCl3, 400 MHz, ppm): δ 8.02 (d, J=8.8 Hz, 1H), 7.95 (d, J=8.4, 1H), 7.71 (d, J=8.0, 1H), 7.58-7.26 (m, 5H), 7.11 (t, J=7.2 Hz, 1H), 6.76 (d, J=8.0 Hz, 1H), 4.17-4.09 (m, 2H), 3.05-2.98 (m, 2H); 13C NMR (CDCl3, 100 MHz, ppm): δ 162.51, 144.46, 137.08, 132.42, 131.43, 130.95, 129.52, 129.14, 128.21, 127.83, 127.61, 121.14, 127.09, 126.88, 126.09, 119.95, 119.28, 116.77, 47.93, 25.57.

Workup

  1. filtrationthe mixture was filtered through a short pad of silica gel
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography on silica gel (5:1 hexanes/EtOAc)
  4. additionThe fractions containing the product (Rf=0.4)
  5. customwere collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-49da699c5651441985dfcb301b1caf96
Source dataset
uspto-grants-2012_05
Patent number
US08183378B2

Reaction notes

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