2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 66597208, compound

HRID 1627759Notes

Reaction equation

HRID 1627759 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:3]=1[CH2:22][C:23]([O:25][CH3:26])=[O:24].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClC1C=CC=CC=1Cl>[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:5]2=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:3]=1[CH2:22][C:23]([O:25][CH3:26])=[O:24]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 66597281HCID 66597281, compound

Product 1

HCID 66597208HCID 66597208, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A suspension of methyl [2-methyl-4-p-tolyl-5,6,7,8-tetrahydro[1]benzothieno [2,3-b]pyridin-3-yl]acetate (0.225 mg; 0.616 mmol) and 2,3-Dichloro-5,6-Dicyanobenzoquinone (0.351 mg; 1.546 mmol) in 1,2-dichlorobenzene (2 mL) was placed in a sealed tube and was irradiated in a microwave oven at 190° C. for 10 minutes. The reaction mixture was then evaporated to dryness under reduced pressure. The residue was suspended in dichloromethane and the solid was filtered through celite. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate (10-30%) in heptane to afford 0.125 g (56%) of the title compound as a pink solid.

Workup

  1. customwas placed in a sealed tube
  2. customwas irradiated in a microwave oven at 190° C. for 10 minutes
  3. customThe reaction mixture was then evaporated to dryness under reduced pressure
  4. filtrationthe solid was filtered through celite
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate (10-30%) in heptane

Sources & evidence

ORD record
ord-f6e5e64470e94630bfbbc85f64e18c4b
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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