2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one

HRID 1031666Notes

Reaction equation

HRID 1031666 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[C:16]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][C:9]2[C:10](=[O:14])[CH2:11][CH2:12][O:13][C:8]=2[CH:7]=1)(=[O:4])=[O:3].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH3:1][S:2]([NH:5][C:6]1[C:16]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][C:9]2[C:10](=[O:14])[CH:11]=[CH:12][O:13][C:8]=2[CH:7]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 10806538HCID 10806538, compound

Product 1

HCID 106164807-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-oneYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 60 ml of dioxane were added 3.33 g of 2,3-dihydro-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one and 3.40 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The mixture was refluxed for 12 hours. After water cooling, the precipitate was removed by filtration. The filtrate was subjected to distillation under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluant: a 5 : 1 mixture of toluene and ethyl acetate) to obtain 2.68 g (yield: 81%) of 7-methylsulfonylamino-6-phenoxy4H-1-benzopyran-4-one [Compound No. 1].

Workup

  1. temperatureThe mixture was refluxed for 12 hours
  2. customAfter water cooling, the precipitate was removed by filtration
  3. distillationThe filtrate was subjected to distillation under reduced pressure
  4. customto remove the solvent
  5. customThe residue was purified by a column chromatography (eluant
  6. additiona 5 : 1 mixture of toluene and ethyl acetate)

Sources & evidence

ORD record
ord-63463992aec744a2beb68b9fa2febce6
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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