2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 136491270, compound

HRID 927030Notes

Reaction equation

HRID 927030 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19]CC3C=CC(OC)=CC=3)=[CH:15][CH:14]=2)=[N:10][O:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.O.C(Cl)Cl.C(OCC)(=O)C>C(Cl)Cl.O>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[C:9]([C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=2)=[N:10][O:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8857Ethyl AcetateHCID 21908982Water methylene chlorideHCID 90203445HCID 90203445, compound

Product 1

HCID 136491270HCID 136491270, compoundYield 101.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of {3-[4-(4-methoxy-benzyloxy)-phenyl]-isoxazol-4-yl}-carbamic acid tert-butyl ester (3.01 g, 7.6 mmol) in CH2Cl2 (80 mL) and water (8 mL) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (5.17 g, 23 mmol). After stirring for 60 h, the reaction mixture was suspended between a water/CH2Cl2 bilayer. The organic phase was removed and the aqueous phase was extracted twice with CH2Cl2. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo to give a deep red oil. [3-(4-Hydroxy-phenyl)-isoxazol-4-yl]-carbamic acid tert-butyl ester (2.14 g, 92%) was isolated by chromatography (1-100% ethyl acetate in hexanes).

Workup

  1. customThe organic phase was removed
  2. extractionthe aqueous phase was extracted twice with CH2Cl2
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a deep red oil

Sources & evidence

ORD record
ord-c6d99385a56747e9a13fb37400011fc7
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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