2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 9890607, compound

HRID 352372Notes

Reaction equation

HRID 352372 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][C:13]([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([N:24]3[CH2:29][C@H:28]([CH3:30])[N:27]([CH3:31])[C@H:26]([CH3:32])[CH2:25]3)[CH:22]=2)[CH2:17][CH2:16]1)=[O:14].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][C:13]([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([N:24]3[CH2:25][C@H:26]([CH3:32])[N:27]([CH3:31])[C@H:28]([CH3:30])[CH2:29]3)[CH:22]=2)[CH:17]=[CH:16]1)=[O:14]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 11408684HCID 11408684, compound

Product 1

HCID 9890607HCID 9890607, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of E8 (1.8 g, 3.86 mmole) in DCM (150 ml) was treated with a solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (908 mg, 4.0 mmole) in DCM (50 ml) and the mixture stirred at room temp. under argon for 20 mins. The mixture was washed with 10% Na2CO3 solution, dried (Na2SO4), and evaporated to a brown oil. Column chromatography on silica gel (eluent 5% MeOH/DCM) afforded the title compound as a yellow semi-solid (1.1 g, 61%), which was converted to its hydrochloride salt as a white solid.

Workup

  1. washThe mixture was washed with 10% Na2CO3 solution
  2. dry with materialdried (Na2SO4)
  3. customevaporated to a brown oil

Sources & evidence

ORD record
ord-5eac00c9a75a40678fa394b0f474aa30
Source dataset
uspto-grants-2004_06
Patent number
US06747030B1

Reaction notes

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