2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 14722319, compound

HRID 1031670Notes

Reaction equation

HRID 1031670 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[C:18]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][C:9]2[C:10](=[O:16])[CH:11]([S:14][CH3:15])[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:18]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][C:9]2[C:10](=[O:16])[C:11]([S:14][CH3:15])=[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 14722454HCID 14722454, compound

Product 1

HCID 14722319HCID 14722319, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

350 mg of 2,3-dihydro-7-methylsulfonylamino-3-methylthio-6-phenoxy-4H-1-benzopyran-4-one and 1.08 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone were refluxed in 14 ml of dioxane for 9 hours. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: a 10 : 1 mixture of toluene and ethyl acetate) to obtain 160 mg (yield: 45.7%) of 7-methylsulfonylamino-3-methylthio-6-phenoxy-4H-1-benzopyran-4-one [Compound No. 4].

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. customThe residue was purified by a column chromatography (eluant
  3. additiona 10 : 1 mixture of toluene and ethyl acetate)

Sources & evidence

ORD record
ord-cdb54e213d034b66925edf472b21d7cb
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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