2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 12020314, compound

HRID 1635036Notes

Reaction equation

[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14](=[O:22])[C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[CH:11][CH:12]=2)[CH:7]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[CH2:6]1)(=[O:4])=[O:3].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14](=[O:22])[C:15]3[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=3)=[CH:11][CH:12]=2)[C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)=[CH:6]1)(=[O:3])=[O:4]

Participants

Conditions

Temperature: 95 °C

Procedure

A solution of 1-methylsulfonyl-3-(3-chlorophenyl)-5-(4-chlorobenzoyl)indoline (350 mg) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (356 mg) in dioxane (6 mL) was refluxed under N2 for about 6 hours and then heated at about 95° C. overnight. The solvent was removed. The residue was purified by column chromatography on silica, eluting with EtOAc/hexane, 1:4. The title compound was obtained as a solid. MS(ES): 443.2, calc. Mw=443.4. Rf=0.38, silica, EtOAc/hexane, 1:2. 195 mg, yield: 56%.

Workup

customThe solvent was removed
customThe residue was purified by column chromatography on silica
washeluting with EtOAc/hexane, 1:4

Sources & evidence

ORD record: ord-8b7e9b07aed1489997343d37555d2e3e
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06509336B1

Reaction notes

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