Sulfuryl chloride → 4,5-Dichloro-1H-indole-2,3-dione

HRID 614899Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[C:5](=[O:11])[NH:6]2.S(Cl)([Cl:16])(=O)=O>>[Cl:1][C:2]1[C:10]([Cl:16])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[C:5](=[O:11])[NH:6]2

Participants

Reactant 2

HCID 24648Sulfuryl chloride

HCID 960474-Chloroisatin

Product 1

HCID 51399804,5-Dichloro-1H-indole-2,3-dioneYield 70%

Procedure

Chlorination of 4-chloroisatin with sulfuryl chloride by the method of B. R. Baker, et al., J. Org. Chem., 17, 149 (1952), gave a 70% yield of the title compound.

Sources & evidence

ORD record: ord-2e9da5e8005d4e098dd9dcb6bdeff0b7
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04146718

Reaction notes

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