2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86634834, compound

HRID 1928558Notes

Reaction equation

HRID 1928558 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[F:15][C:16]([F:48])([F:47])[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][C@H:33]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[NH:32]1)(=[O:19])=[O:18]>C(Cl)Cl>[F:48][C:16]([F:15])([F:47])[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][C@H:33]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[N:32]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86634835HCID 86634835, compound

Product 1

HCID 86634834HCID 86634834, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Powdered 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) (908 mg, 4.0 mmol) was added to a solution of 5 (2.033 g, 4.21 mmol) in CH2Cl2 (20 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 (9:1 hexanes/EtOAc) to yield the title product 6 (1.65 g, 86% yield) as a solid. 1H NMR (CDCl3, 400 MHz, ppm): δ 8.03-7.93 (m, 2H), 7.54-7.12 (m, 12H), 6.86-6.79 (m, 1H), 5.04-4.94 (m, 1H), 3.29-3.06 (m, 2H); HRMS calcd for C26H19F3NO3S+1 (M+1): 482.1038. found: 482.1032.

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 (9:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-f5b83f79cdc24020975afe1f7581b3fc
Source dataset
uspto-grants-2012_05
Patent number
US08183378B2

Reaction notes

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